2-oxo-2-(per'ACH'-1H-indol-3-yl)acetyl [Cl,Br,I] by Asch

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Date

179 substances in Reaxys

2016-08-01 07h:43m:41s (EST)

[Cl,Br,I]

O ACH

1. Query

ACH

ACH N

ACH ACH

ACH

Search as: As drawn, No mixtures, No isotopes, No charges, No radicals

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Reaxys ID 147693 View in Reaxys

1/179 CAS Registry Number: 22980-09-2 Chemical Name: indolyl-3-glyoxylyl chloride; 2-(3-indolyl)-2-oxoacetyl chloride Linear Structure Formula: C10H6O2NCl Molecular Formula: C10H6ClNO2 Molecular Weight: 207.616 Type of Substance: heterocyclic InChI Key: FPEGGKCNMYDNMW-UHFFFAOYSA-N Note:

O O

Substance Label (25) Label References ITE-1

Patent; AHR PHARMACEUTICALS, INC.; SONG, Jiasheng; ZHANG, Suoming; LI, Guodong; YANG, Luqing; (40 pag.); WO2016/40553; (2016); (A1) English, View in Reaxys

Fresneda, Pilar M.; Bleda, Juan Antonio; Sanz, Miguel Angel; Molina, Pedro; Synlett; nb. 10; (2007); p. 1541 - 1544, View in Reaxys; Mielczarek, Marcins; Devakaram, Ruth V.; Ma, Cong; Yang, Xiao; Kandemir, Hakan; Purwono, Bambang; Black, David Stc.; Griffith, Renate; Lewis, Peter J.; Kumar, Naresh; Organic and Biomolecular Chemistry; vol. 12; nb. 18; (2014); p. 2882 - 2894, View in Reaxys; Singh, Palwinder; Prasher, Parteek; Dhillon, Parvirti; Bhatti, Rajbir; European Journal of Medicinal Chemistry; vol. 97; (2015); p. 104 - 123, View in Reaxys

Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 1368, View in Reaxys; Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys

Dethe, Dattatraya H.; Ranjan, Alok; RSC Advances; vol. 3; nb. 45; (2013); p. 23692 - 23703, View in Reaxys; Mielczarek, Marcin; Thomas, Ruth V.; Ma, Cong; Kandemir, Hakan; Yang, Xiao; Bhadbhade, Mohan; Black, David Stc.; Griffith, Renate; Lewis, Peter J.; Kumar, Naresh; Bioorganic and Medicinal Chemistry; vol. 23; nb. 8; (2015); p. 1763 - 1775, View in Reaxys

Taliani, Sabrina; Trincavelli, Maria Letizia; Cosimelli, Barbara; Laneri, Sonia; Severi, Elda; Barresi, Elisabetta; Pugliesi, Isabella; Daniele, Simona; Giacomelli, Chiara; Greco, Giovanni; Novellino, Ettore; Martini, Claudia; Da Settimo, Federico; European Journal of Medicinal Chemistry; vol. 69; (2013); p. 331 337, View in Reaxys; Mir, Fauzia; Shafi, Syed; Zaman; Kalia, Nitin Pal; Rajput, Vikrant S.; Mulakayala, Chaitanya; Mulakayala, Naveen; Khan, Inshad A.; Alam; European Journal of Medicinal Chemistry; vol. 76; (2014); p. 274 - 283, View in Reaxys

Prasher, Parteek; Pooja; Singh, Palwinder; Bioorganic and Medicinal Chemistry; vol. 22; nb. 5; (2014); p. 1642 - 1648, View in Reaxys

Singh, Palwinder; Pooja; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 5; (2013); p. 1433 - 1437, View in Reaxys

Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys; Patent; UNIVERSITE JOSEPH FOURIER; DENIS, Jean-Noël; JOLIVALT, Claude, Marcelle; MAURIN, Max, Maurin, Louis; BURCHAK, Olga, Nikolaevna; WO2013/14104; (2013); (A1) English, View in Reaxys

Sallem, Wafa; Serradji, Nawal; Dereuddre-Bosquet, Nathalie; Dive, Georges; Clayette, Pascal; Heymans, Francoise; Bioorganic and Medicinal Chemistry; vol. 14; nb. 23; (2006); p. 7999 - 8013, View in Reaxys; Gardner, Christopher R.; Cheung, Belamy B.; Koach, Jessica; Black, David Stc.; Marshall, Glenn M.; Kumar, Naresh; Bioorganic and Medicinal Chemistry; vol. 20; nb. 23; (2012); p. 6877 6884, View in Reaxys

Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys

10a

Guinchard, Xavier; Vallee, Yannick; Denis, Jean-Noel; Journal of Organic Chemistry; vol. 72; nb. 10; (2007); p. 3972 - 3975, View in Reaxys

(I), R=R'=H

Gupta, Leena; Talwar, Archna; Nishi; Palne, Shraddha; Gupta, Suman; Chauhan, Prem M.S.; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 14; (2007); p. 4075 - 4079, View in Reaxys

Guinchara, Xavier; Vallee, Yannick; Denis, Jean-Noel; Organic Letters; vol. 9; nb. 19; (2007); p. 3761 3764, View in Reaxys

Hashem, Md. Abul; Sultana, Israt; Hai, Abdul; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 38; nb. 7; (1999); p. 789 - 794, View in Reaxys; Wang, Jingsong; Le, Nhut; Heredia,

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Alonso; Song, Haijing; Redfield, Robert; Wang, Lai-Xi; Organic and Biomolecular Chemistry; vol. 3; nb. 9; (2005); p. 1781 - 1786, View in Reaxys 4a

Aubry, Carine; Patel, Asma; Mahale, Sachin; Chaudhuri, Bhabatosh; Marechal, Jean-Didier; Sutcliffe, Michael J.; Jenkins, Paul R.; Tetrahedron Letters; vol. 46; nb. 9; (2005); p. 1423 - 1425, View in Reaxys

Krayushkin; Sedishev; Yarovenko; Zavarzin; Vorontsova; Starikova; Nabatov; Russian Journal of Organic Chemistry; vol. 41; nb. 9; (2005); p. 1349 - 1353, View in Reaxys

Krayushkin; Yarovenko; Sedishev; Zavarzin; Vorontsova; Starikova; Russian Journal of Organic Chemistry; vol. 41; nb. 6; (2005); p. 875 - 883, View in Reaxys

Miyake; Yakushijin; Horne; Organic letters; vol. 2; nb. 14; (2000); p. 2121 - 2123, View in Reaxys; Sears, R. Bryan; Carpenter, Russell A.; Whitlock, Christine R.; Molecules; vol. 10; nb. 2; (2005); p. 488 - 491, View in Reaxys

Battaglia, Sandra; Boldrini, Enrico; Da Settimo, Federico; Dondio, Giulio; La Motta, Concettina; Marini, Anna Maria; Primofiore, Giampaolo; European Journal of Medicinal Chemistry; vol. 34; nb. 2; (1999); p. 93 - 105, View in Reaxys; Grzywacz, Pawel; Sicinski, Rafal R.; DeLuca, Hector F.; Heterocycles; vol. 60; nb. 5; (2003); p. 1219 - 1224, View in Reaxys

Intermediate 9

Patent; Kadow, John F.; Xue, Qiufen May; Wang, Tao; Zhang, Zhongxing; Meanwell, Nicholas A.; US2003/236277; (2003); (A1) English, View in Reaxys

Garg, Neil K.; Sarpong, Richmond; Stoltz, Brian M.; Journal of the American Chemical Society; vol. 124; nb. 44; (2002); p. 13179 - 13184, View in Reaxys

Miyake, Fumiko Y; Yakushijin, Kenichi; Horne, David A; Organic letters; vol. 4; nb. 6; (2002); p. 941 - 943, View in Reaxys

Jiang, Biao; Gu, Xiao-Hui; Bioorganic and Medicinal Chemistry; vol. 8; nb. 2; (2000); p. 363 - 371, View in Reaxys

Jiang, Biao; Gu, Xiao-Hui; Heterocycles; vol. 53; nb. 7; (2000); p. 1559 - 1568, View in Reaxys

Faul, Margaret M.; Winneroski, Leonard L.; Krumrich, Christine A.; Journal of Organic Chemistry; vol. 63; nb. 17; (1998); p. 6053 - 6058, View in Reaxys

Patent-Specific Data (3) Location in Patent References Page/Page column

Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys; Patent; BristolMyers Squibb Company; Walker, Michael A.; Sorenson, Margaret E.; Naidu, B. Narasimhulu; Peese, Kevin; Johnson, Barry L.; Patel, Manoj; US2013/210857; (2013); (A1) English, View in Reaxys Patent; LECTUS THERAPEUTICS LIMITED; WO2009/19508; (2009); (A1) English, View in Reaxys Patent; Ruah, Sara Hadida; Hazlewood, Anna; Grootenhuis, Peter; Zhou, Jinglan; US2007/264196; (2007); (A1) English, View in Reaxys

Melting Point (9) 1 of 9

Melting Point [°C]

116 - 118

Melting Point [°C]

134 - 135

Comment (Melting Point)

Decomposition

Hashem, Md. Abul; Sultana, Israt; Hai, Abdul; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 38; nb. 7; (1999); p. 789 - 794, View in Reaxys 3 of 9

Melting Point [°C]

134

Patent; Ciba-Geigy AG; FR2303541; (1976); DE2609289; (1976); Chem.Abstr.; vol. 86; nb. 16538, View in Reaxys; Patent; Ciba-Geigy AG; DD124386; (1977); DE2609289; (1976); Chem.Abstr.; vol. 86; nb. 16538, View in Reaxys 4 of 9

Melting Point [°C]

123 - 124

Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys 5 of 9

Melting Point [°C]

136

Lingens; Lange; Justus Liebigs Annalen der Chemie; vol. 738; (1970); p. 46,47,51, View in Reaxys 6 of 9

Melting Point [°C]

128

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Neumeyer; Moyer; Leonard; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 450 - 452, View in Reaxys 7 of 9

Melting Point [°C]

138

Solvent (Melting Point)

diethyl ether

Millich; Becker; Journal of Organic Chemistry; vol. 23; (1958); p. 1096,1097, View in Reaxys 8 of 9

Melting Point [°C]

135

Solvent (Melting Point)

benzene

Comment (Melting Point)

Decomp.

Shaw et al.; Journal of Organic Chemistry; vol. 23; (1958); p. 1171,1176, View in Reaxys 9 of 9

Melting Point [°C]

135 - 136

Comment (Melting Point)

Decomp.

Kharasch; Kane; Brown; Journal of the American Chemical Society; vol. 62; (1940); p. 2243, View in Reaxys Crystal Property Description (8) Colour & Other Location Properties yellow

Page/Page column 20

References Patent; AHR PHARMACEUTICALS, INC.; SONG, Jiasheng; ZHANG, Suoming; LI, Guodong; YANG, Luqing; (40 pag.); WO2016/40553; (2016); (A1) English, View in Reaxys

orange

Manivannan, Ramalingam; Satheshkumar, Angupillai; El-Mossalamy, El-Sayed H.; Al-Harbi, Laila M.; Kosa, Samia A.; Elango, Kuppanagounder P.; New Journal of Chemistry; vol. 39; nb. 5; (2015); p. 3936 - 3947, View in Reaxys

red

Mielczarek, Marcins; Devakaram, Ruth V.; Ma, Cong; Yang, Xiao; Kandemir, Hakan; Purwono, Bambang; Black, David Stc.; Griffith, Renate; Lewis, Peter J.; Kumar, Naresh; Organic and Biomolecular Chemistry; vol. 12; nb. 18; (2014); p. 2882 - 2894, View in Reaxys

yellow

Gardner, Christopher R.; Cheung, Belamy B.; Koach, Jessica; Black, David Stc.; Marshall, Glenn M.; Kumar, Naresh; Bioorganic and Medicinal Chemistry; vol. 20; nb. 23; (2012); p. 6877 - 6884, View in Reaxys; Dethe, Dattatraya H.; Ranjan, Alok; RSC Advances; vol. 3; nb. 45; (2013); p. 23692 - 23703, View in Reaxys

yellow

Paragraph 0136

Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys

yellow

Page/Page column 23

Patent; UNIVERSITE JOSEPH FOURIER; DENIS, Jean-Noël; JOLIVALT, Claude, Marcelle; MAURIN, Max, Maurin, Louis; BURCHAK, Olga, Nikolaevna; WO2013/14104; (2013); (A1) English, View in Reaxys

yellow

Hashem, Md. Abul; Sultana, Israt; Hai, Abdul; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 38; nb. 7; (1999); p. 789 - 794, View in Reaxys; Sears, R. Bryan; Carpenter, Russell A.; Whitlock, Christine R.; Molecules; vol. 10; nb. 2; (2005); p. 488 - 491, View in Reaxys; Wang, Jingsong; Le, Nhut; Heredia, Alonso; Song, Haijing; Redfield, Robert; Wang, Lai-Xi; Organic and Biomolecular Chemistry; vol. 3; nb. 9; (2005); p. 1781 - 1786, View in Reaxys; Takhi, Mohamed; Singh, Gurpreet; Murugan; Thaplyyal, Nirvesh; Maitra, Soma; Bhaskarreddy; Amarnath; Mallik, Arundhuti; Harisudan; Trivedi, Ravi Kumar; Sreenivas; Selvakumar; Iqbal, Javed; Bioorganic and Medicinal Chemistry Letters; vol. 18; nb. 18; (2008); p. 5150 5155, View in Reaxys; Aubry, Carine; Wilson, A. James; Emmerson, Daniel; Murphy, Emma; Chan, Yu Yam; Dickens, Michael P.; Garcia, Marcos D.; Jenkins, Paul R.; Mahale, Sachin; Chaudhuri, Bhabatosh; Bioorganic and Medicinal Chemistry; vol. 17; nb. 16; (2009); p. 6073 - 6084, View in Reaxys; Guinchara, Xavier; Vallee, Yannick; Denis, Jean-Noel; Organic Letters; vol. 9; nb. 19; (2007); p. 3761 - 3764, View in Reaxys; Kamila, Sukanta; Ankati, Haribabu; Biehl, Edward R.; Arkivoc; vol. 2011; nb. 9; (2011); p. 94 - 104, View in Reaxys Rusterholz et al.; Journal of Medicinal Chemistry; vol. 19; (1976); p. 99,100, View in Reaxys

Decomposition (1) 1 of 1

Decomposition [°C]

116 - 117

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Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Aubry, Carine; Wilson, A. James; Emmerson, Daniel; Murphy, Emma; Chan, Yu Yam; Dickens, Michael P.; Garcia, Marcos D.; Jenkins, Paul R.; Mahale, Sachin; Chaudhuri, Bhabatosh; Bioorganic and Medicinal Chemistry; vol. 17; nb. 16; (2009); p. 6073 - 6084, View in Reaxys; Mielczarek, Marcins; Devakaram, Ruth V.; Ma, Cong; Yang, Xiao; Kandemir, Hakan; Purwono, Bambang; Black, David Stc.; Griffith, Renate; Lewis, Peter J.; Kumar, Naresh; Organic and Biomolecular Chemistry; vol. 12; nb. 18; (2014); p. 2882 - 2894, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Millich; Becker; Journal of Organic Chemistry; vol. 23; (1958); p. 1096,1097, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)

References

liquid chromatog- Page/Page colraphy mass spec- umn 20 trometry (LCMS); spectrum

Patent; AHR PHARMACEUTICALS, INC.; SONG, Jiasheng; ZHANG, Suoming; LI, Guodong; YANG, Luqing; (40 pag.); WO2016/40553; (2016); (A1) English, View in Reaxys

Reaxys ID 162759 View in Reaxys

2/179 CAS Registry Number: 22980-10-5 Chemical Name: (2-methyl-3-indolyl)glyoxyloyl chloride; 2methylindole-3-glyoxylylchloride; 2-methylindoleglyoxylyl chloride; (2-methyl-indol-3-yl)-oxo-acetyl chloride; (2-Methyl-indol-3yl)-glyoxyloylchlorid; 2-methyl-indole-3-glyoxyloyl chloride; (2Methyl-indolyl-3)-glyoxylsaeurechlorid Linear Structure Formula: C9H8NCOCOCl Molecular Formula: C11H8ClNO2 Molecular Weight: 221.643 Type of Substance: heterocyclic InChI Key: MBAONGDWDAMRIY-UHFFFAOYSA-N Note:

O O

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Substance Label (7) Label References 1

Kolotaev; Belen'kii; Kononikhin; Krayushkin; Russian Chemical Bulletin; vol. 55; nb. 5; (2006); p. 892 897, View in Reaxys

Purohit, M. G.; Badiger, G. R.; Kalaskar, N. J.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 34; nb. 9; (1995); p. 796 - 801, View in Reaxys

acid chloride to 2b

Guan, Xiangming; Borchardt, Ronald T.; Tetrahedron Letters; vol. 35; nb. 19; (1994); p. 3013 - 3016, View in Reaxys

10f

Da Settimo; Marini; Primofiore; Subissi; Farmaco; vol. 46; nb. 2; (1991); p. 357 - 367, View in Reaxys

5, R=H, R'=CH3

Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys

IIIf

Kumar; Agarwal; Nath; et al.; Journal of Heterocyclic Chemistry; vol. 18; nb. 6; (1981); p. 1269 - 1271, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

147 - 147.5

Neumeyer; Moyer; Leonard; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 450 - 452, View in Reaxys

Reaxys ID 396067 View in Reaxys

3/179 CAS Registry Number: 59022-69-4 Linear Structure Formula: C11H8ClNO2 Molecular Formula: C11H8ClNO2 Molecular Weight: 221.643 Type of Substance: heterocyclic InChI Key: GKWQILOPRWVNTD-UHFFFAOYSA-N Note:

O O

Substance Label (2) Label References 14 (X=7-Me)

Contour-Galcera, Marie-Odile; Sidhu, Alban; Plas, Pascale; Roubert, Pierre; Bioorganic and Medicinal Chemistry Letters; vol. 15; nb. 15; (2005); p. 3555 - 3559, View in Reaxys

18c

Kornet; Thio; Journal of Medicinal Chemistry; vol. 19; (1976); p. 892,897, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

176 - 177

Kornet; Thio; Journal of Medicinal Chemistry; vol. 19; (1976); p. 892,897, View in Reaxys

Reaxys ID 476959 View in Reaxys

4/179 CAS Registry Number: 16382-38-0 Chemical Name: 1-methylindole-3-glyoxylyl chloride; (1-methyl-1H-indol-3-yl)-oxo-acetyl chloride; 1-methyl-α-oxo-3-indoleacetyl chloride; 2-(1-methyl-1H-indol-3-yl)-2-oxoacetyl chloride; (1-methyl-indol-3-yl)-oxo-acetyl chloride; 1-methyl-α-oxo-3-indoleacetyl chloride; (1-methyl-1H-indol-3-yl)-oxo-acetylchloride Linear Structure Formula: C11H8NO2Cl Molecular Formula: C11H8ClNO2 Molecular Weight: 221.643 Type of Substance: heterocyclic InChI Key: SLZAXHIJSANSSM-UHFFFAOYSA-N Note:

O O

Substance Label (4)

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Label

References

26-a

Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; JACHMANN, Markus; WAKAMATSU, Takayuki; ANRYU, Mitsuharu; WO2012/33225; (2012); (A1) English, View in Reaxys

Roy, Sudipta; Gribble, Gordon W.; Synthetic Communications; vol. 37; nb. 11; (2007); p. 1879 - 1886, View in Reaxys

Roy, Sudipta; Eastman, Alan; Gribble, Gordon W.; Tetrahedron; vol. 62; nb. 33; (2006); p. 7838 - 7845, View in Reaxys

Roy, Sudipta; Roy, Sujata; Gribble, Gordon W.; Organic Letters; vol. 8; nb. 21; (2006); p. 4975 - 4977, View in Reaxys

Related Structure (1) References Lingens; Lange; Justus Liebigs Annalen der Chemie; vol. 738; (1970); p. 46,47,51, View in Reaxys Melting Point (2) 1 of 2

Melting Point [°C]

91 - 92

Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys 2 of 2

Melting Point [°C]

113

Lingens; Lange; Justus Liebigs Annalen der Chemie; vol. 738; (1970); p. 46,47,51, View in Reaxys Crystal Property Description (1) References Buzas et al.; Bulletin de la Societe Chimique de France; (1960); p. 644, View in Reaxys Decomposition (1) 1 of 1

Buzas et al.; Bulletin de la Societe Chimique de France; (1960); p. 644, View in Reaxys

Further Information (1) Description (Fur- References ther Information) Further information

Taborsky et al.; Journal of Medicinal Chemistry; vol. 10; (1967); p. 403,404, View in Reaxys

Solubility (MCS) (1) 1 of 1

Comment (Solubility (MCS))

Loesl. in Ae.

Buzas et al.; Bulletin de la Societe Chimique de France; (1960); p. 644, View in Reaxys NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)

1H NMR (CDCI3)δ ppm: 8.40-8.38 (1H, m) , 8.15 (1H, s), 7.43-7.40 (3H, m) , 3.91 (3H, s)

Location

Page/Page column 299

Comment (NMR Spectroscopy)

Signals given

Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; JACHMANN, Markus; WAKAMATSU, Takayuki; ANRYU, Mitsuharu; WO2012/33225; (2012); (A1) English, View in Reaxys

Reaxys ID 5527527 View in Reaxys

5/179 Linear Structure Formula: C11H8ClNO2 Molecular Formula: C11H8ClNO2 Molecular Weight: 221.643 Type of Substance: heterocyclic InChI Key: KLSRVPOKCADARD-UHFFFAOYSA-N

O O

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Note:

Reaxys ID 5527874 View in Reaxys

6/179 Linear Structure Formula: C11H8ClNO2 Molecular Formula: C11H8ClNO2 Molecular Weight: 221.643 Type of Substance: heterocyclic InChI Key: FVELJKVORCPYSW-UHFFFAOYSA-N Note:

O O

Reaxys ID 6804138 View in Reaxys

7/179 CAS Registry Number: 115956-14-4 Chemical Name: (5-methyl-1H-indol-3-yl)-oxoacetyl chloride; 5-methyl-3-indolylglyoxylyl chloride Linear Structure Formula: C9H8NCOCOCl Molecular Formula: C11H8ClNO2 Molecular Weight: 221.643 Type of Substance: heterocyclic InChI Key: MMKGFWKUIRFAJH-UHFFFAOYSA-N Note:

O O

Substance Label (2) Label References 4d

acid chloride to 2c Guan, Xiangming; Borchardt, Ronald T.; Tetrahedron Letters; vol. 35; nb. 19; (1994); p. 3013 - 3016, View in Reaxys Crystal Property Description (1) Colour & Other References Properties yellow

Decomposition (1) 1 of 1

Decomposition [°C]

155

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Description (NMR Spec- Chemical shifts troscopy)

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Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

Reaxys ID 9398299 View in Reaxys HO

8/179 Linear Structure Formula: C10H6ClNO3 Molecular Formula: C10H6ClNO3 Molecular Weight: 223.616 Type of Substance: heterocyclic InChI Key: WUPRPGHPECCJPC-UHFFFAOYSA-N Note:

O O

Reaxys ID 10345659 View in Reaxys

9/179 Chemical Name: (7-hydroxy-1H-indol-3-yl)oxoacetyl chloride Linear Structure Formula: C10H6ClNO3 Molecular Formula: C10H6ClNO3 Molecular Weight: 223.616 Type of Substance: heterocyclic InChI Key: LZRIJNJLGZWXQT-UHFFFAOYSA-N Note:

OH NH

O O

Substance Label (1) Label References 11

Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys

Crystal Property Description (1) Colour & Other References Properties orange - red

Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys

Reaxys ID 19577011 View in Reaxys OH

10/179 Cl

Linear Structure Formula: C10H6ClNO3 Molecular Formula: C10H6ClNO3 Molecular Weight: 223.616 InChI Key: RRCBDVJNNBOKPP-UHFFFAOYSA-N Note:

Reaxys ID 20863728 View in Reaxys

11/179

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Linear Structure Formula: C10H6ClNO3 Molecular Formula: C10H6ClNO3 Molecular Weight: 223.616 InChI Key: KITZCWNCPUATFA-UHFFFAOYSA-N Note:

HO NH

Reaxys ID 398904 View in Reaxys

12/179 CAS Registry Number: 3828-10-2 Chemical Name: 2-(6-fluoro-1H-indol-3-yl)-2-oxoacetyl chloride; 6-fluoroindol-3-ylglyoxalyl chloride; (6-fluoro-indol-3-yl)-oxoacetyl chloride; 6-fluoroindole-3-glyoxylyl chloride; 6-fluoroindoleglyoxyl chloride; 6-Fluor-3-chloroxalyl-indol Linear Structure Formula: C10H5ClFNO2 Molecular Formula: C10H5ClFNO2 Molecular Weight: 225.607 Type of Substance: heterocyclic InChI Key: HRDNIVYOZFIBFP-UHFFFAOYSA-N Note:

O O

Substance Label (3) Label References 8g

Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys

14 (X=6-F)

Contour-Galcera, Marie-Odile; Sidhu, Alban; Plas, Pascale; Roubert, Pierre; Bioorganic and Medicinal Chemistry Letters; vol. 15; nb. 15; (2005); p. 3555 - 3559, View in Reaxys

13c

Blair; Kurrasch-Orbaugh; Marona-Lewicka; Gumbay; Watts; Barker; Nichols; Journal of Medicinal Chemistry; vol. 43; nb. 24; (2000); p. 4701 - 4710, View in Reaxys

Patent-Specific Data (1) Prophetic ComLocation in Patent References pound prophetic product

Paragraph 0148-0149

Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

250

Bentov,M. et al.; Journal of the Chemical Society; (1962); p. 2825 - 2827, View in Reaxys

Reaxys ID 478187 View in Reaxys

13/179 CAS Registry Number: 2192-28-1 Chemical Name: 4-fluoro-α-oxo-1H-indole-3-acetyl chloride; 4fluoro-2-(1H-indol-3-yl)-2-oxoacetyl chloride; 2-(4-fluoro-1H-indol-3-yl)-2-oxoacetyl chloride; (4-fluoro-1H-indol-3-yl)-oxo-acetyl chloride; 4-Fluor-3-chlorglyoxyloyl-indol Linear Structure Formula: C10H5ClFNO2 Molecular Formula: C10H5ClFNO2 Molecular Weight: 225.607 Type of Substance: heterocyclic InChI Key: FKRRABHXUWVCEV-UHFFFAOYSA-N Note:

O F

Substance Label (2) Label References A-In-5

Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/158394; (2009); (A1) English, View in Reaxys

Wang, Jingsong; Le, Nhut; Heredia, Alonso; Song, Haijing; Redfield, Robert; Wang, Lai-Xi; Organic and Biomolecular Chemistry; vol. 3; nb. 9; (2005); p. 1781 - 1786, View in Reaxys

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Patent-Specific Data (2) References Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/158394; (2009); (A1) English, View in Reaxys Patent; Bristol-Myers Squibb Company; US2007/287712; (2007); (A1) English, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

252

Bentov,M. et al.; Israel Journal of Chemistry; vol. 2; (1964); p. 25 - 28, View in Reaxys Crystal Property Description (2) Colour & Other Location Properties yellow

References

supporting information

Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758, View in Reaxys

yellow

Patent; Bristol-Myers Squibb Company; US2007/249624; (2007); (A1) English, View in Reaxys

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H-NMR

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

12.62; 8.37; 7.36; 7.26; 6.99

Kind of signal

s, 1H; d, J=3.5 Hz, 1H; m, 1H; m, 1H; dd, J=7.8, 10.9 Hz, 1H

(400 MHz, DMSO-d6) δ 12.62 (s, 1H), 8.37 (d, J=3.5 Hz, 1H), 7.36 (m, 1H), 7.26 (m, 1H), 6.99 (dd, J=7.8, 10.9 Hz, 1H)

Patent; Bristol-Myers Squibb Company; US2007/249624; (2007); (A1) English, View in Reaxys Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry) LCMS (Liquid chromatography mass spectrometry)

References

Molecular peak

Patent; Bristol-Myers Squibb Company; US2007/249624; (2007); (A1) English, View in Reaxys

Reaxys ID 478189 View in Reaxys

14/179 CAS Registry Number: 3828-09-9 Chemical Name: 2-(5-fluoro-1H-indol-3-yl)-2-oxoacetyl chloride; (5-fluoro-1H-indol-3-yl)-oxoacetyl chloride; 5-Fluor-3-indolylglyoxylylchlorid Linear Structure Formula: C10H5ClFNO2 Molecular Formula: C10H5ClFNO2 Molecular Weight: 225.607 Type of Substance: heterocyclic InChI Key: OTOJFEFGCPXZGW-UHFFFAOYSA-N Note:

NH F

O O

Substance Label (3) Label References 8f

Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys

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Bsp.264

Patent; Sterling Drug; US3217011; (1965); Chem.Abstr.; vol. 64; nb. 12649, View in Reaxys

Patent-Specific Data (1) Prophetic ComLocation in Patent References pound prophetic product

Paragraph 0148-0149

Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

160 - 170

Patent; Sterling Drug; US3217011; (1965); Chem.Abstr.; vol. 64; nb. 12649, View in Reaxys Crystal Property Description (1) Colour & Other References Properties yellow

Decomposition (1) 1 of 1

Decomposition [°C]

145 - 146

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

19F

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

282

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Reaxys ID 404149 View in Reaxys

15/179 CAS Registry Number: 65923-30-0 Chemical Name: (4-cyano-indol-3-yl)-oxo-acetyl chloride; 4Cyano-3-indolglyoxylyl-chlorid Linear Structure Formula: C11H5ClN2O2 Molecular Formula: C11H5ClN2O2 Molecular Weight: 232.626 Type of Substance: heterocyclic InChI Key: CFGJUPOREMDDEQ-UHFFFAOYSA-N Note:

O N

Substance Label (1) Label References XI

Ananthanarayanan,C.V. et al.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 15; (1977); p. 710 - 714, View in Reaxys

Melting Point (1) 1 of 1

Ananthanarayanan,C.V. et al.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 15; (1977); p. 710 - 714, View in Reaxys

IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Ananthanarayanan,C.V. et al.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 15; (1977); p. 710 - 714, View in Reaxys

Reaxys ID 8770173 View in Reaxys

16/179 Chemical Name: 2-(5-cyano-1H-indol-3-yl)-2-oxoacetyl chloride Linear Structure Formula: C11H5ClN2O2 Molecular Formula: C11H5ClN2O2 Molecular Weight: 232.626 Type of Substance: heterocyclic InChI Key: BUVZNSWLNKOAGH-UHFFFAOYSA-N Note:

N O

Substance Label (1) Label References intermediate 34

Patent; JANSSEN PHARMACEUTICA N.V.; WO2006/32631; (2006); (A1) English, View in Reaxys

Crystal Property Description (1) Colour & Other References Properties red

Kamila, Sukanta; Ankati, Haribabu; Biehl, Edward R.; Arkivoc; vol. 2011; nb. 9; (2011); p. 94 - 104, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy)

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Kamila, Sukanta; Ankati, Haribabu; Biehl, Edward R.; Arkivoc; vol. 2011; nb. 9; (2011); p. 94 - 104, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Kamila, Sukanta; Ankati, Haribabu; Biehl, Edward R.; Arkivoc; vol. 2011; nb. 9; (2011); p. 94 - 104, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Kamila, Sukanta; Ankati, Haribabu; Biehl, Edward R.; Arkivoc; vol. 2011; nb. 9; (2011); p. 94 - 104, View in Reaxys

Reaxys ID 9400407 View in Reaxys

17/179 CAS Registry Number: 881204-76-8 Linear Structure Formula: C11H5ClN2O2 Molecular Formula: C11H5ClN2O2 Molecular Weight: 232.626 Type of Substance: heterocyclic InChI Key: VGSWLOJCJWFAOX-UHFFFAOYSA-N Note:

N NH

O O

Reaxys ID 399039 View in Reaxys

18/179 Chemical Name: 2-Ethyl-3-(chlor-oxalyl)-indol Linear Structure Formula: C12H10ClNO2 Molecular Formula: C12H10ClNO2 Molecular Weight: 235.67 Type of Substance: heterocyclic InChI Key: OOJOKLQTMSWPBC-UHFFFAOYSA-N Note:

O O

Reaxys ID 3651556 View in Reaxys

19/179 CAS Registry Number: 117196-94-8 Chemical Name: 1,2-Dimethyl-α-oxo-1H-indole-3-acetyl chloride; (1,2-dimethyl-3-indolyl)glyoxyloyl chloride; 1,2-dimethylindol-3-ylglyoxylyl chloride; 1,2-dimethyl-α-oxo-3-indoleacetyl chloride; 1,2-dimethyl-α-oxo-3-indoleacetyl chloride Linear Structure Formula: C12H10ClNO2 Molecular Formula: C12H10ClNO2 Molecular Weight: 235.67 Type of Substance: heterocyclic InChI Key: GZZOOXRMPOCEBK-UHFFFAOYSA-N Note:

O O

Substance Label (6) Label References

14/63

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Calvert, Matthew B.; Sperry, Jonathan; Tetrahedron Letters; vol. 53; nb. 40; (2012); p. 5426 - 5429, View in Reaxys

Kolotaev; Belen'kii; Kononikhin; Krayushkin; Russian Chemical Bulletin; vol. 55; nb. 5; (2006); p. 892 897, View in Reaxys

2 (tab. run 1)

Bit, Rino A.; Crackett, Peter H.; Harris, William; Hill, Christopher H.; Tetrahedron Letters; vol. 34; nb. 35; (1993); p. 5623 - 5626, View in Reaxys

10g

Da Settimo; Marini; Primofiore; Subissi; Farmaco; vol. 46; nb. 2; (1991); p. 357 - 367, View in Reaxys

5, R=R'=CH3

Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys

IIIg

Melting Point (2) 1 of 2

Melting Point [°C]

Kolotaev; Belen'kii; Kononikhin; Krayushkin; Russian Chemical Bulletin; vol. 55; nb. 5; (2006); p. 892 - 897, View in Reaxys 2 of 2

Melting Point [°C]

60 - 62

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Ciganek; Schubert; Journal of Organic Chemistry; vol. 60; nb. 14; (1995); p. 4629 - 4634, View in Reaxys; Kolotaev; Belen'kii; Kononikhin; Krayushkin; Russian Chemical Bulletin; vol. 55; nb. 5; (2006); p. 892 - 897, View in Reaxys 2 of 2

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Kolotaev; Belen'kii; Kononikhin; Krayushkin; Russian Chemical Bulletin; vol. 55; nb. 5; (2006); p. 892 - 897, View in Reaxys

Reaxys ID 4867290 View in Reaxys

20/179 CAS Registry Number: 143137-57-9 Chemical Name: 1,7-dimethyl-α-oxo-3-indoleacetyl chloride; 1,7-dimethyl-α-oxo-3-indoleacetyl chloride Linear Structure Formula: C12H10ClNO2 Molecular Formula: C12H10ClNO2 Molecular Weight: 235.67 Type of Substance: heterocyclic InChI Key: TUTLGFVRDACFMZ-UHFFFAOYSA-N Note:

O O

Reaxys ID 4867348 View in Reaxys

21/179

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CAS Registry Number: 202807-67-8 Chemical Name: (1,5-dimethyl-1H-indol-3-yl)-oxo-acetyl chloride Linear Structure Formula: C12H10ClNO2 Molecular Formula: C12H10ClNO2 Molecular Weight: 235.67 Type of Substance: heterocyclic InChI Key: LGVGGGFVASYZIB-UHFFFAOYSA-N Note:

O O

Reaxys ID 4867590 View in Reaxys

22/179 Linear Structure Formula: C12H10ClNO2 Molecular Formula: C12H10ClNO2 Molecular Weight: 235.67 Type of Substance: heterocyclic InChI Key: XPQWBCDGZXPBHN-UHFFFAOYSA-N Note:

O O

Reaxys ID 5536367 View in Reaxys

23/179 CAS Registry Number: 111478-91-2 Linear Structure Formula: C12H10ClNO2 Molecular Formula: C12H10ClNO2 Molecular Weight: 235.67 Type of Substance: heterocyclic InChI Key: DQFFTJWDMSCSHY-UHFFFAOYSA-N Note:

O O

Reaxys ID 8622562 View in Reaxys

24/179 CAS Registry Number: 172896-14-9 Linear Structure Formula: C12H10ClNO2 Molecular Formula: C12H10ClNO2 Molecular Weight: 235.67 Type of Substance: heterocyclic InChI Key: DJFJDHYMNXBWEU-UHFFFAOYSA-N Note:

O O

Reaxys ID 9397312 View in Reaxys

25/179 Linear Structure Formula: C12H10ClNO2 Molecular Formula: C12H10ClNO2 Molecular Weight: 235.67 Type of Substance: heterocyclic InChI Key: KQVXJVSXJPZUGA-UHFFFAOYSA-N Note:

O O

Reaxys ID 15442545 View in Reaxys

26/179

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Linear Structure Formula: C12H10ClNO2 Molecular Formula: C12H10ClNO2 Molecular Weight: 235.67 InChI Key: RSUCXQRUMFUPLX-UHFFFAOYSA-N Note:

O Cl O N

Reaxys ID 19577014 View in Reaxys

27/179 CAS Registry Number: 1388070-52-7 Linear Structure Formula: C12H10ClNO2 Molecular Formula: C12H10ClNO2 Molecular Weight: 235.67 InChI Key: WJKZVQOHTYNKAF-UHFFFAOYSA-N Note:

Reaxys ID 20773785 View in Reaxys

28/179 Linear Structure Formula: C12H10ClNO2 Molecular Formula: C12H10ClNO2 Molecular Weight: 235.67 InChI Key: MVUVOLJGACESKG-UHFFFAOYSA-N Note:

Reaxys ID 22921388 View in Reaxys

29/179 CAS Registry Number: 61751-68-6 Linear Structure Formula: C12H10ClNO2 Molecular Formula: C12H10ClNO2 Molecular Weight: 235.67 InChI Key: APCXOFWZJSLJSP-UHFFFAOYSA-N Note:

Reaxys ID 29581904 View in Reaxys

30/179 Linear Structure Formula: C12H10ClNO2 Molecular Formula: C12H10ClNO2 Molecular Weight: 235.67 InChI Key: DNCNRNRZHFUBLB-UHFFFAOYSA-N Note:

O Cl O

Reaxys ID 176546 View in Reaxys

31/179 CAS Registry Number: 68104-22-3 Chemical Name: (6-methoxy-1H-indol-3-yl)(oxo)acetyl chloride; 2-(3-indolyl)-2-oxoacetyl chloride; (6-methoxy-indol-3-yl)oxoacetyl chloride; (6-Methoxy-indol-3-yl)-glyoxyloylchlorid; 6methoxy-indole-3-glyoxylyl chloride; 6-methoxyindole-3-glyoxylyl chloride; 6-methoxyindole-3-glyoxyl chloride Linear Structure Formula: C11H8NO3Cl Molecular Formula: C11H8ClNO3

O O

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Molecular Weight: 237.642 Type of Substance: heterocyclic InChI Key: DXPOTHDZYYMXIQ-UHFFFAOYSA-N Note: Substance Label (4) Label References 19

Gitto, Rosaria; De Luca, Laura; Ferro, Stefania; Russo, Emilio; De Sarro, Giovambattista; Chisari, Mariangela; Ciranna, Lucia; Alvarez-Builla, Julio; Alajarin, Ramon; Buemi, Maria Rosa; Chimirri, Alba; Bioorganic and Medicinal Chemistry; vol. 22; nb. 3; (2014); p. 1040 - 1048, View in Reaxys

10c

Guinchard, Xavier; Vallee, Yannick; Denis, Jean-Noel; Journal of Organic Chemistry; vol. 72; nb. 10; (2007); p. 3972 - 3975, View in Reaxys

interm. to 18b

Leonard, John; Hague, Andrew B.; Jones, Martin F.; Tetrahedron Letters; vol. 38; nb. 17; (1997); p. 3071 3074, View in Reaxys

Feldman, Paul L.; Rapoport, Henry; Synthesis; nb. 9; (1986); p. 735 - 737, View in Reaxys

Melting Point (2) 1 of 2

Melting Point [°C]

125 - 128

Comment (Melting Point)

Decomp.nach Wiedererstarren F: 150-165grad.

Woodward et al.; Tetrahedron; vol. 2; (1958); p. 1,32, View in Reaxys 2 of 2

Melting Point [°C]

150

Patent; Upjohn Co.; US2813128; (1955), View in Reaxys Crystal Property Description (2) Colour & Other References Properties yellow

Patent; Glacera Contour, Marie-Odile; Sidhu, Alban; Roubert, Pierre; Thurieau, Christophe; US2005/154039; (2005); (A1) English, View in Reaxys

rot

Woodward et al.; Tetrahedron; vol. 2; (1958); p. 1,32, View in Reaxys

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

NMR 1H (DMSO-d6, 400 MHz) δ: 12.19 (s, 1H, NH); 8.27 (s, 1H, arom.); 8.01-7.99 (d, J=8.7 Hz, 1H, arom.); 7.02 (s, 1H, arom.); 6.90-6.87 (d, J=8.7 Hz, 1H, arom.); 3.79 (s, 1H, OCH3).

Comment (NMR Spectroscopy)

Signals given

Patent; Glacera Contour, Marie-Odile; Sidhu, Alban; Roubert, Pierre; Thurieau, Christophe; US2005/154039; (2005); (A1) English, View in Reaxys

Reaxys ID 190033 View in Reaxys

32/179 CAS Registry Number: 2426-19-9 Chemical Name: (5-methoxy-1H-indol-3-yl)oxoacetyl chloride; 5-methoxyindole-3-glyoxyloyl chloride; 2-(5-methoxy-1H-indol-3-yl)-2-oxoacetyl chloride; (5-methoxyindol-3-yl)glyoxylyl chloride; 5-methoxyindolyl-3-ylglyoxylyl chloride; 5-methoxyindol-3-yl-glyoxalyl chloride; 5-methoxy-3-indoleglyoxyloyl chloride Linear Structure Formula: C11H8NO3Cl Molecular Formula: C11H8ClNO3 Molecular Weight: 237.642

NH O

O O

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Type of Substance: heterocyclic InChI Key: BXRAIGUKJHRMRI-UHFFFAOYSA-N Note: Substance Label (16) Label References 18

Spadoni, Gilberto; Bedini, Annalida; Bartolucci, Silvia; Pala, Daniele; Mor, Marco; Riccioni, Teresa; Borsini, Franco; Cabri, Walter; Celona, Diana; Marzi, Mauro; Tarzia, Giorgio; Rivara, Silvia; Minetti, Patrizia; European Journal of Medicinal Chemistry; vol. 80; (2014); p. 8 - 35, View in Reaxys

Singh, Palwinder; Pooja; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 5; (2013); p. 1433 - 1437, View in Reaxys

Vermeulen, Erik S; van Smeden, Marjan; Schmidt, Anne W; Sprouse, Jeffrey S; Wikstroem, Hakan V; Grol, Cor J; Journal of medicinal chemistry; vol. 47; nb. 22; (2004); p. 5451 - 5466, View in Reaxys

Bergman, Jan; Janosik, Tomasz; Johnsson, Ann-Louise; Synthesis; nb. 4; (1999); p. 580 - 582, View in Reaxys

interm. to 18a

Leonard, John; Hague, Andrew B.; Jones, Martin F.; Tetrahedron Letters; vol. 38; nb. 17; (1997); p. 3071 3074, View in Reaxys

Da Settimo; Marini; Primofiore; Farmaco; vol. 50; nb. 5; (1995); p. 321 - 326, View in Reaxys

10e

Da Settimo; Marini; Primofiore; Subissi; Farmaco; vol. 46; nb. 2; (1991); p. 357 - 367, View in Reaxys

4 (R=OMe)

Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys

IIIe

Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys; da Settimo; Primofiore; Marini; Mori; Franzone; Cirillo; Reboani; Farmaco, Edizione Scientifica; vol. 42; nb. 1; (1987); p. 17 - 26, View in Reaxys

Primofiore; Marini; Da Settimo; Franzone; Mason; Reboani; Cirillo; European Journal of Medicinal Chemistry; vol. 23; nb. 4; (1988); p. 397 - 401, View in Reaxys

II (R=OCH3)

Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys

S.28,29

Patent; Ciba-Geigy AG; DD124386; (1977); DE2609289; (1976); Chem.Abstr.; vol. 86; nb. 16538, View in Reaxys

Shaw; Wright; Milne; Biomedical mass spectrometry; vol. 4; nb. 6; (1977); p. 348 - 353, View in Reaxys

S.bei 3, S.18

Patent; Ciba-Geigy AG; FR2303541; (1976); DE2609289; (1976); Chem.Abstr.; vol. 86; nb. 16538, View in Reaxys

Melting Point (7) 1 of 7

Melting Point [°C]

123 - 126

Gynther, Jukka; Peura, Pekka; Salmi, Seija; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 39; nb. 10; (1985); p. 849 - 860, View in Reaxys 2 of 7

Melting Point [°C]

132 - 134

Melting Point [°C]

127 - 128

Shaw; Wright; Milne; Biomedical mass spectrometry; vol. 4; nb. 6; (1977); p. 348 - 353, View in Reaxys 4 of 7

Melting Point [°C]

118 - 119

Neumeyer; Moyer; Leonard; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 450 - 452, View in Reaxys 5 of 7

Melting Point [°C]

126 - 127

Solvent (Melting Point)

diethyl ether

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Bertaccini; Vitali; Farmaco, Edizione Scientifica; vol. 22; (1967); p. 229,231, View in Reaxys 6 of 7

Melting Point [°C]

134

Takatori; Takashima; Yakugaku Zasshi; vol. 83; (1963); p. 795,798, View in Reaxys 7 of 7

Melting Point [°C]

130

Kralt,T. et al.; Recueil des Travaux Chimiques des Pays-Bas; vol. 80; (1961); p. 313 - 324, View in Reaxys; Ballantine et al.; Journal of the Chemical Society; (1957); p. 2222,2226, View in Reaxys Crystal Property Description (2) Colour & Other References Properties orange

Kamila, Sukanta; Ankati, Haribabu; Biehl, Edward R.; Arkivoc; vol. 2011; nb. 9; (2011); p. 94 - 104, View in Reaxys

orangerot

Ballantine et al.; Journal of the Chemical Society; (1957); p. 2222,2226, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Kamila, Sukanta; Ankati, Haribabu; Biehl, Edward R.; Arkivoc; vol. 2011; nb. 9; (2011); p. 94 - 104, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Kamila, Sukanta; Ankati, Haribabu; Biehl, Edward R.; Arkivoc; vol. 2011; nb. 9; (2011); p. 94 - 104, View in Reaxys IR Spectroscopy (3) 1 of 3

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Kamila, Sukanta; Ankati, Haribabu; Biehl, Edward R.; Arkivoc; vol. 2011; nb. 9; (2011); p. 94 - 104, View in Reaxys 2 of 3

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Vermeulen, Erik S; van Smeden, Marjan; Schmidt, Anne W; Sprouse, Jeffrey S; Wikstroem, Hakan V; Grol, Cor J; Journal of medicinal chemistry; vol. 47; nb. 22; (2004); p. 5451 - 5466, View in Reaxys 3 of 3

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

3195 - 706 1/cm

Bergman, Jan; Janosik, Tomasz; Johnsson, Ann-Louise; Synthesis; nb. 4; (1999); p. 580 - 582, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry)

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spectrum

Gynther, Jukka; Peura, Pekka; Salmi, Seija; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 39; nb. 10; (1985); p. 849 - 860, View in Reaxys Shaw; Wright; Milne; Biomedical mass spectrometry; vol. 4; nb. 6; (1977); p. 348 - 353, View in Reaxys

Reaxys ID 404076 View in Reaxys

33/179 CAS Registry Number: 50656-47-8 Chemical Name: 7-methoxyindole-3-glyoxyl chloride; 7-Methoxy-3-indol-glyoxylchlorid Linear Structure Formula: C11H8NO3Cl Molecular Formula: C11H8ClNO3 Molecular Weight: 237.642 Type of Substance: heterocyclic InChI Key: HOFMRJTYEWFTOE-UHFFFAOYSA-N Note:

O NH

O O

Substance Label (1) Label References 21

Yates et al.; Journal of the American Chemical Society; vol. 95; (1973); p. 7842,7849, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

133 - 134

Yates et al.; Journal of the American Chemical Society; vol. 95; (1973); p. 7842,7849, View in Reaxys Crystal Property Description (1) Colour & Other References Properties orange

Rege, Pankaj D.; Tian, Yuan; Corey; Organic Letters; vol. 8; nb. 14; (2006); p. 3117 - 3120, View in Reaxys

Reaxys ID 9395412 View in Reaxys

34/179 Chemical Name: 4-methoxy-2-(1H-indol-3-yl)-2-oxoacetyl chloride Linear Structure Formula: C11H8NO3Cl Molecular Formula: C11H8ClNO3 Molecular Weight: 237.642 Type of Substance: heterocyclic InChI Key: CGRFHUOVDZKOSY-UHFFFAOYSA-N Note:

O O

Reaxys ID 9400096 View in Reaxys

35/179 Linear Structure Formula: C11H8ClNO3 Molecular Formula: C11H8ClNO3 Molecular Weight: 237.642 Type of Substance: heterocyclic InChI Key: YZWQIYCYSYRSOO-UHFFFAOYSA-N Note:

O HO

Reaxys ID 21451919 View in Reaxys

36/179

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CAS Registry Number: 69111-71-3 Linear Structure Formula: C11H8ClNO3 Molecular Formula: C11H8ClNO3 Molecular Weight: 237.642 InChI Key: BZKFQUGEFMNEKK-UHFFFAOYSA-N Note:

O N

O O

Use (1) Laboratory Use and Handling unstable at room temperature

References Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys

Reaxys ID 11112637 View in Reaxys

37/179

CAS Registry Number: 396091-17-1 Linear Structure Formula: C11H7ClFNO2 Molecular Formula: C11H7ClFNO2 Molecular Weight: 239.633 InChI Key: SDHMSWQRQVPHFP-UHFFFAOYSA-N Note:

Cl N

Reaxys ID 13675964 View in Reaxys

38/179 Chemical Name: (6-fluoro-1-methyl-1H-indol-3-yl)-oxo-acetyl chloride Linear Structure Formula: C11H7ClFNO2 Molecular Formula: C11H7ClFNO2 Molecular Weight: 239.633 InChI Key: LSMNIAWTHOCTKL-UHFFFAOYSA-N Note:

N O F Cl O

Reaxys ID 13676221 View in Reaxys

39/179 Chemical Name: (4-fluoro-1-methyl-1H-indol-3-yl)-oxo-acetyl chloride Linear Structure Formula: C11H7ClFNO2 Molecular Formula: C11H7ClFNO2 Molecular Weight: 239.633 InChI Key: SHAGXXOFOOLLBH-UHFFFAOYSA-N Note:

N O Cl O

Reaxys ID 22921391 View in Reaxys O

40/179 O

Linear Structure Formula: C11H7ClFNO2 Molecular Formula: C11H7ClFNO2 Molecular Weight: 239.633 InChI Key: HLPVUDVUXAVFFV-UHFFFAOYSA-N Note:

F NH

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Reaxys ID 398054 View in Reaxys

41/179 CAS Registry Number: 65610-54-0 Chemical Name: (2-chloro-indol-3-yl)-oxo-acetyl chloride Linear Structure Formula: C10H5Cl2NO2 Molecular Formula: C10H5Cl2NO2 Molecular Weight: 242.061 Type of Substance: heterocyclic InChI Key: JQIOPBYGUUQYEJ-UHFFFAOYSA-N Note:

NH Cl O O

Substance Label (1) Label References 19

Chan, Fiona; Magnus, Philip; McIver, Edward G.; Tetrahedron Letters; vol. 41; nb. 6; (2000); p. 835 - 838, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

140 - 145

Bergmann et al.; Journal of Heterocyclic Chemistry; vol. 14; (1977); p. 1122,1131, View in Reaxys

Reaxys ID 4314317 View in Reaxys

42/179 CAS Registry Number: 883-55-6 Chemical Name: 2-(5-chloro-1H-indol-3-yl)-2-oxoacetyl chloride; 5-chloro-α-oxo-3-indoleacetyl chloride; (5-chloro-1H-indol-3-yl)-oxoacetyl chloride; 3-(5-chloroindolyl)glyoxylic acid chloride; 5-chloro-α-oxo-3-indoleacetyl chloride Linear Structure Formula: C8H5NCOCOCl2 Molecular Formula: C10H5Cl2NO2 Molecular Weight: 242.061 Type of Substance: heterocyclic InChI Key: GRNSNOSVGJPSHX-UHFFFAOYSA-N Note:

NH Cl

O O

Substance Label (5) Label References 8d

Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys

14 (X=5-Cl)

Contour-Galcera, Marie-Odile; Sidhu, Alban; Plas, Pascale; Roubert, Pierre; Bioorganic and Medicinal Chemistry Letters; vol. 15; nb. 15; (2005); p. 3555 - 3559, View in Reaxys

Gilbert, Eric J.; Ziller, Joseph W.; Van Vranken, David L.; Tetrahedron; vol. 53; nb. 48; (1997); p. 16553 16564, View in Reaxys

Patent-Specific Data (1) Prophetic ComLocation in Patent References pound prophetic product

Paragraph 0148-0149

Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys

Crystal Property Description (1) Colour & Other References Properties yellow

Aubry, Carine; Wilson, A. James; Emmerson, Daniel; Murphy, Emma; Chan, Yu Yam; Dickens, Michael P.; Garcia, Marcos D.; Jenkins, Paul R.; Mahale, Sachin; Chaudhuri, Bhabatosh; Bioorganic and Medicinal Chemistry; vol. 17; nb. 16; (2009); p. 6073 - 6084, View in Reaxys; Kamila, Sukanta; Ankati, Haribabu; Biehl, Edward R.; Arkivoc; vol. 2011; nb. 9; (2011); p. 94 - 104, View in Reaxys

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Decomposition (1) 1 of 1

Decomposition [°C]

155

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

Reaxys ID 7531840 View in Reaxys

43/179 CAS Registry Number: 252979-02-5 Chemical Name: 2-(6-chloro-1H-indol-3-yl)-2-oxoacetyl chloride Linear Structure Formula: C10H5Cl2NO2 Molecular Formula: C10H5Cl2NO2 Molecular Weight: 242.061 Type of Substance: heterocyclic InChI Key: UJKKIPZDZUKMPF-UHFFFAOYSA-N Note:

O O

Substance Label (2) Label References 8e

Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys

(I), R=H, R'=Cl

Gupta, Leena; Talwar, Archna; Nishi; Palne, Shraddha; Gupta, Suman; Chauhan, Prem M.S.; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 14; (2007); p. 4075 - 4079, View in Reaxys

Patent-Specific Data (1) Prophetic ComLocation in Patent References pound prophetic product

Paragraph 0148-0149

Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys

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Reaxys ID 9262163 View in Reaxys

44/179 CAS Registry Number: 863289-28-5 Linear Structure Formula: C8H5NCOCOCl2 Molecular Formula: C10H5Cl2NO2 Molecular Weight: 242.061 Type of Substance: heterocyclic InChI Key: VQFRPJBOAXPNCA-UHFFFAOYSA-N Note:

Cl NH

O O

Substance Label (1) Label References 14 (X=7-Cl)

Contour-Galcera, Marie-Odile; Sidhu, Alban; Plas, Pascale; Roubert, Pierre; Bioorganic and Medicinal Chemistry Letters; vol. 15; nb. 15; (2005); p. 3555 - 3559, View in Reaxys

Reaxys ID 11112623 View in Reaxys

45/179

Linear Structure Formula: C13H8ClNO2 Molecular Formula: C13H8ClNO2 Molecular Weight: 245.665 InChI Key: KGKXWVDVSPHWFF-UHFFFAOYSA-N Note:

O Cl

Reaxys ID 410729 View in Reaxys

46/179 CAS Registry Number: 100398-99-0 Chemical Name: (4-Cyanmethyl-indolyl-3)-glyoxylsaeurechlorid Linear Structure Formula: C12H7ClN2O2 Molecular Formula: C12H7ClN2O2 Molecular Weight: 246.653 Type of Substance: heterocyclic InChI Key: AALBLRCZGDHVTM-UHFFFAOYSA-N Note:

O O

Melting Point (1) 1 of 1

Melting Point [°C]

106 - 110

Plieninger,H.; Mueller,W.; Chemische Berichte; vol. 93; (1960); p. 2024 - 2028, View in Reaxys

Reaxys ID 10437626 View in Reaxys

47/179 Linear Structure Formula: C12H7ClN2O2 Molecular Formula: C12H7ClN2O2 Molecular Weight: 246.653 Type of Substance: heterocyclic InChI Key: NCDOJVJTZTVWHU-UHFFFAOYSA-N Note:

N N

O O

Substance Label (1) Label References 15

Roy, Sudipta; Eastman, Alan; Gribble, Gordon W.; Tetrahedron; vol. 62; nb. 33; (2006); p. 7838 - 7845, View in Reaxys

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Reaxys ID 13676604 View in Reaxys

48/179 Chemical Name: (5-cyano-1-methyl-1H-indol-3-yl)-oxo-acetyl chloride Linear Structure Formula: C12H7ClN2O2 Molecular Formula: C12H7ClN2O2 Molecular Weight: 246.653 InChI Key: VOARXEAVUAYRLE-UHFFFAOYSA-N Note:

N O

Reaxys ID 13677046 View in Reaxys

49/179 CAS Registry Number: 202745-66-2 Chemical Name: (6-cyano-1-methyl-1H-indol-3-yl)-oxo-acetyl chloride; (6-cyano-1-methyl-1H-indol-3-yl)glyoxylyl chloride Linear Structure Formula: C12H7ClN2O2 Molecular Formula: C12H7ClN2O2 Molecular Weight: 246.653 InChI Key: WEFXNTLSKCMIME-UHFFFAOYSA-N Note:

N O N Cl O

Reaxys ID 404591 View in Reaxys

50/179 CAS Registry Number: 73031-18-2 Chemical Name: 5-Acetylindol-3-ylglyoxylsaeurechlorid Linear Structure Formula: C12H8ClNO3 Molecular Formula: C12H8ClNO3 Molecular Weight: 249.653 Type of Substance: heterocyclic InChI Key: VGWKJYZTEXGUHT-UHFFFAOYSA-N Note:

NH O O O

Crystal Property Description (1) References Eryschew et al.; Trudy Instituta - Moskovskii Institut Tonkoi Khimicheskoi Tekhnologii imeni M. V. Lomonosova; vol. 94; (1977); p. 42,43; Chem.Abstr.; vol. 92; nb. 128647, View in Reaxys

Reaxys ID 4454639 View in Reaxys

51/179 Linear Structure Formula: C12H8ClNO3 Molecular Formula: C12H8ClNO3 Molecular Weight: 249.653 Type of Substance: heterocyclic InChI Key: RANQFSZBXWPBKI-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References 14

Kim, Phieo Ta; Guilard, Roger; Dodey, Pierre; Sornay, Roland; Journal of Heterocyclic Chemistry; vol. 18; (1981); p. 1365 - 1371, View in Reaxys

Reaxys ID 10161516 View in Reaxys

52/179

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Linear Structure Formula: C12H8ClNO3 Molecular Formula: C12H8ClNO3 Molecular Weight: 249.653 Type of Substance: heterocyclic InChI Key: DBGILIBWRDMFMR-UHFFFAOYSA-N Note:

O N

O O

Reaxys ID 8623568 View in Reaxys

53/179 Linear Structure Formula: C13H12ClNO2 Molecular Formula: C13H12ClNO2 Molecular Weight: 249.697 Type of Substance: heterocyclic InChI Key: ANOFZOPHASJFRR-UHFFFAOYSA-N Note:

O O

Reaxys ID 14389461 View in Reaxys O

54/179 Linear Structure Formula: C13H12ClNO2 Molecular Formula: C13H12ClNO2 Molecular Weight: 249.697 InChI Key: LEVYFWNBUZMOGE-UHFFFAOYSA-N Note:

Cl O

Reaxys ID 23171848 View in Reaxys F

55/179 Cl

CAS Registry Number: 389628-22-2 Linear Structure Formula: C11H4ClFN2O2 Molecular Formula: C11H4ClFN2O2 Molecular Weight: 250.616 InChI Key: XTHDSLLREWKXDP-UHFFFAOYSA-N Note:

Substance Label (2) Label References 33

Yeung, Kap-Sun; Qiu, Zhilei; Yin, Zhiwei; Trehan, Ashok; Fang, Haiquan; Pearce, Bradley; Yang, Zheng; Zadjura, Lisa; D'Arienzo, Celia J.; Riccardi, Keith; Shi, Pei-Yong; Spicer, Timothy P.; Gong, YiFei; Browning, Marc R.; Hansel, Steven; Santone, Kenneth; Barker, Jonathan; Coulter, Thomas; Lin, Ping-Fang; Meanwell, Nicholas A.; Kadow, John F.; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 1; (2013); p. 203 - 208, View in Reaxys

Yeung, Kap-Sun; Qiu, Zhilei; Yang, Zheng; Zadjura, Lisa; D'Arienzo, Celia J.; Browning, Marc R.; Hansel, Steven; Huang, Xiaohua Stella; Eggers, Betsy J.; Riccardi, Keith; Lin, Ping-Fang; Meanwell, Nicholas A.; Kadow, John F.; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 1; (2013); p. 209 - 212, View in Reaxys

Reaxys ID 7481247 View in Reaxys

56/179

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CAS Registry Number: 175988-05-3 Linear Structure Formula: C12H7ClFNO2 Molecular Formula: C12H7ClFNO2 Molecular Weight: 251.644 Type of Substance: heterocyclic InChI Key: PKLISZBZMMRXFV-UHFFFAOYSA-N Note:

NH F O O

Substance Label (1) Label References 16

Gharat; Martin; Journal of Heterocyclic Chemistry; vol. 33; nb. 1; (1996); p. 197 - 201, View in Reaxys

Reaxys ID 191761 View in Reaxys

57/179

CAS Registry Number: 100123-60-2 Chemical Name: (6-ethoxy-indol-3-yl)-oxoacetyl chloride; (6Aethoxy-indol-3-yl)-glyoxyloylchlorid; <6-Ethoxy-indolyl-(3)>glyoxylsaeure-chlorid; 6-Ethoxy-indol-3-glyoxylsaeurchlorid Linear Structure Formula: C12H10ClNO3 Molecular Formula: C12H10ClNO3 Molecular Weight: 251.669 Type of Substance: heterocyclic InChI Key: SNPSTXKBZMOEGE-UHFFFAOYSA-N Note:

O O

Melting Point (2) 1 of 2

Kralt,T. et al.; Recueil des Travaux Chimiques des Pays-Bas; vol. 80; (1961); p. 313 - 324, View in Reaxys

2 of 2

Melting Point [°C]

125 - 126

Adlerova,E. et al.; Collection of Czechoslovak Chemical Communications; vol. 25; (1960); p. 784 - 796, View in Reaxys; Protiva et al.; Naturwissenschaften; vol. 46; (1959); p. 263, View in Reaxys Crystal Property Description (1) Colour & Other References Properties rot

Adlerova,E. et al.; Collection of Czechoslovak Chemical Communications; vol. 25; (1960); p. 784 - 796, View in Reaxys; Protiva et al.; Naturwissenschaften; vol. 46; (1959); p. 263, View in Reaxys

Reaxys ID 407789 View in Reaxys

58/179 CAS Registry Number: 16382-43-7 Chemical Name: 5-methoxy-1-methylindole-3-glyoxylyl chloride; (5-methoxy-1-methyl-1H-indol-3-yl)-oxo-acetyl chloride; 1methyl-5-methoxy-α-oxo-3-indoleacetyl chloride; 1-methyl-5methoxy-α-oxo-3-indoleacetyl chloride; 5-Methoxy-1-methylindole-3-glyoxyloyl-chloride Linear Structure Formula: C12H10ClNO3 Molecular Formula: C12H10ClNO3 Molecular Weight: 251.669 Type of Substance: heterocyclic InChI Key: ZJUGTCYOQGGMJF-UHFFFAOYSA-N Note:

N O

O O

Further Information (1) Description (Fur- References ther Information) Further information

Taborsky et al.; Journal of Medicinal Chemistry; vol. 10; (1967); p. 403,404, View in Reaxys

NMR Spectroscopy (2)

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1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Davis, Peter D.; Hill, Christopher H.; Lawton, Geoffrey; Nixon, John S.; Wilkinson, Sandra E.; et al.; Journal of Medicinal Chemistry; vol. 35; nb. 1; (1992); p. 177 - 184, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Davis, Peter D.; Hill, Christopher H.; Lawton, Geoffrey; Nixon, John S.; Wilkinson, Sandra E.; et al.; Journal of Medicinal Chemistry; vol. 35; nb. 1; (1992); p. 177 - 184, View in Reaxys

Reaxys ID 3550393 View in Reaxys

59/179 CAS Registry Number: 1026388-93-1 Chemical Name: 2-(5-methoxy-2-methyl-1H-indol-3-yl)-2-oxoacetyl chloride Linear Structure Formula: C12H10ClNO3 Molecular Formula: C12H10ClNO3 Molecular Weight: 251.669 Type of Substance: heterocyclic InChI Key: WFOKFPROUZEACN-UHFFFAOYSA-N Note:

NH O

O O

Substance Label (1) Label References 2c

Crystal Property Description (1) Colour & Other References Properties red

Kamila, Sukanta; Ankati, Haribabu; Biehl, Edward R.; Arkivoc; vol. 2011; nb. 9; (2011); p. 94 - 104, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Kamila, Sukanta; Ankati, Haribabu; Biehl, Edward R.; Arkivoc; vol. 2011; nb. 9; (2011); p. 94 - 104, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy)

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Kamila, Sukanta; Ankati, Haribabu; Biehl, Edward R.; Arkivoc; vol. 2011; nb. 9; (2011); p. 94 - 104, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Kamila, Sukanta; Ankati, Haribabu; Biehl, Edward R.; Arkivoc; vol. 2011; nb. 9; (2011); p. 94 - 104, View in Reaxys

Reaxys ID 4869204 View in Reaxys

60/179 CAS Registry Number: 202807-56-5 Chemical Name: (6-methoxy-1-methyl-1H-indol-3-yl)-oxo-acetyl chloride Linear Structure Formula: C12H10ClNO3 Molecular Formula: C12H10ClNO3 Molecular Weight: 251.669 Type of Substance: heterocyclic InChI Key: YIGVDZAHSTVYDX-UHFFFAOYSA-N Note:

O O

Reaxys ID 4872106 View in Reaxys

61/179 Linear Structure Formula: C12H10ClNO3 Molecular Formula: C12H10ClNO3 Molecular Weight: 251.669 Type of Substance: heterocyclic InChI Key: WKWRDTCAEMPROB-UHFFFAOYSA-N Note:

O N

O O

Reaxys ID 4872162 View in Reaxys

62/179 CAS Registry Number: 143137-55-7 Chemical Name: (4-methoxy-1-methyl-1H-indol-3-yl)-oxo-acetyl chloride; 1-methyl-4-methoxy-α-oxo-3-indoleacetyl chloride; 1-methyl-4-methoxy-α-oxo-3-indoleacetyl chloride Linear Structure Formula: C12H10ClNO3 Molecular Formula: C12H10ClNO3 Molecular Weight: 251.669 Type of Substance: heterocyclic InChI Key: MBMZNVBRAUARDX-UHFFFAOYSA-N Note:

O O

Reaxys ID 5544982 View in Reaxys

63/179 Linear Structure Formula: C12H10ClNO3 Molecular Formula: C12H10ClNO3 Molecular Weight: 251.669 Type of Substance: heterocyclic InChI Key: GRPVJPLPIWSCPT-UHFFFAOYSA-N Note:

NH O

O O

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Reaxys ID 9265462 View in Reaxys

64/179 Linear Structure Formula: C12H10NO3Cl Molecular Formula: C12H10ClNO3 Molecular Weight: 251.669 Type of Substance: heterocyclic InChI Key: BLBYEJUNTCASEW-UHFFFAOYSA-N Note:

NH O

O O

Reaxys ID 9403407 View in Reaxys

65/179

Linear Structure Formula: C12H10ClNO3 Molecular Formula: C12H10ClNO3 Molecular Weight: 251.669 Type of Substance: heterocyclic InChI Key: VICOMLVZWWGYAT-UHFFFAOYSA-N Note:

O O

Reaxys ID 13730104 View in Reaxys

66/179 Chemical Name: (1-methoxymethyl-1H-indol-3-yl)-oxo-acetyl chloride; (1-methoxymethyl-1H-indol-3-yl)-oxo acetyl chloride Linear Structure Formula: C12H10ClNO3 Molecular Formula: C12H10ClNO3 Molecular Weight: 251.669 InChI Key: FXRVCVSYAPUTTG-UHFFFAOYSA-N Note:

O O N

Cl O

Reaxys ID 19577012 View in Reaxys

67/179 CAS Registry Number: 1442439-41-9 Linear Structure Formula: C12H10ClNO3 Molecular Formula: C12H10ClNO3 Molecular Weight: 251.669 InChI Key: GOYMIDZDGQBSSF-UHFFFAOYSA-N Note:

Reaxys ID 19577013 View in Reaxys

68/179 Cl

Linear Structure Formula: C12H10ClNO3 Molecular Formula: C12H10ClNO3 Molecular Weight: 251.669 InChI Key: LYJPBKPZYWDBHK-UHFFFAOYSA-N Note:

NH O

Reaxys ID 413570 View in Reaxys

69/179

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CAS Registry Number: 6953-35-1 Chemical Name: 2-(5-nitro-1H-indol-3-yl)-2-oxoacetyl chloride; 5-nitroindol-3-ylglyoxylyl chloride; (5-nitro-indol-3-yl)-oxo-acetyl chloride Linear Structure Formula: C10H5ClN2O4 Molecular Formula: C10H5ClN2O4 Molecular Weight: 252.614 Type of Substance: heterocyclic InChI Key: ABMDPBTXKRNTSH-UHFFFAOYSA-N Note:

NH O

N O

O O

Substance Label (3) Label References 9

Too, Kathleen; Brown, Daniel M.; Holliger, Philipp; Loakes, David; Collection of Czechoslovak Chemical Communications; vol. 71; nb. 6; (2006); p. 899 - 911, View in Reaxys

Crystal Property Description (1) Colour & Other References Properties yellow

Kamila, Sukanta; Ankati, Haribabu; Biehl, Edward R.; Arkivoc; vol. 2011; nb. 9; (2011); p. 94 - 104, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Kamila, Sukanta; Ankati, Haribabu; Biehl, Edward R.; Arkivoc; vol. 2011; nb. 9; (2011); p. 94 - 104, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Kamila, Sukanta; Ankati, Haribabu; Biehl, Edward R.; Arkivoc; vol. 2011; nb. 9; (2011); p. 94 - 104, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Kamila, Sukanta; Ankati, Haribabu; Biehl, Edward R.; Arkivoc; vol. 2011; nb. 9; (2011); p. 94 - 104, View in Reaxys

Reaxys ID 14564327 View in Reaxys

70/179

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CAS Registry Number: 1388061-97-9 Linear Structure Formula: C10H5ClN2O4 Molecular Formula: C10H5ClN2O4 Molecular Weight: 252.614 InChI Key: UGAINDWVLPSNFB-UHFFFAOYSA-N Note:

O O

Cl N O

O NH

Reaxys ID 18920708 View in Reaxys O

71/179 Cl

O O

Linear Structure Formula: C10H5ClN2O4 Molecular Formula: C10H5ClN2O4 Molecular Weight: 252.614 InChI Key: CDSJWOCIQGILPG-UHFFFAOYSA-N Note:

Reaxys ID 18920709 View in Reaxys

72/179 Cl

Linear Structure Formula: C10H5ClN2O4 Molecular Formula: C10H5ClN2O4 Molecular Weight: 252.614 InChI Key: QWXBZXIGHOSJLB-UHFFFAOYSA-N Note:

NH O

Crystal Property Description (1) Colour & Other Location Properties yellow

References

Page/Page column 86

Patent; BRISTOL-MYERS SQUIBB COMPANY; WANG, Tao; ZHANG, Zhongxing; YIN, Zhiwei; KADOW, John, F.; MEANWELL, Nicholas, A.; WO2012/19003; (2012); (A1) English, View in Reaxys

Reaxys ID 402650 View in Reaxys

73/179 CAS Registry Number: 37093-88-2 Linear Structure Formula: C11H8ClNO2S Molecular Formula: C11H8ClNO2S Molecular Weight: 253.709 Type of Substance: heterocyclic InChI Key: CKUVLWBSAOYYCO-UHFFFAOYSA-N Note:

NH S O O

Melting Point (1) 1 of 1

Melting Point [°C]

130 - 135

Bourdais,J. et al.; Chimica Therapeutica; vol. 6; (1971); p. 120 - 125, View in Reaxys

Reaxys ID 5033876 View in Reaxys

74/179 Linear Structure Formula: C11H8ClNO2S Molecular Formula: C11H8ClNO2S Molecular Weight: 253.709 Type of Substance: heterocyclic InChI Key: BOKMHWRANRHCQT-UHFFFAOYSA-N Note:

O S

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Substance Label (1) Label References 21b

Kline, Toni B.; Benington, Frederick; Morin, Richard D.; Beaton, John M.; Journal of Medicinal Chemistry; vol. 25; nb. 8; (1982); p. 908 - 913, View in Reaxys

Reaxys ID 9128575 View in Reaxys

75/179 CAS Registry Number: 228098-50-8 Chemical Name: 5-methylthio-indol-3-ylglyoxyloyl chloride Linear Structure Formula: C11H8ClNO2S Molecular Formula: C11H8ClNO2S Molecular Weight: 253.709 Type of Substance: heterocyclic InChI Key: DCNNHWWXEAOEFL-UHFFFAOYSA-N Note:

NH S

O O

Melting Point (1) 1 of 1

Melting Point [°C]

129 - 133

Comment (Melting Point)

Decomposition

Glennon, Richard A.; Bondarev, Mikhail; Roth, Bryan; Medicinal Chemistry Research; vol. 9; nb. 2; (1999); p. 108 - 117, View in Reaxys Crystal Property Description (1) Colour & Other References Properties yellow

Glennon, Richard A.; Bondarev, Mikhail; Roth, Bryan; Medicinal Chemistry Research; vol. 9; nb. 2; (1999); p. 108 - 117, View in Reaxys

Reaxys ID 8843569 View in Reaxys

76/179 Linear Structure Formula: C11H7ClFNO3 Molecular Formula: C11H7ClFNO3 Molecular Weight: 255.633 Type of Substance: heterocyclic InChI Key: GYEABRCIFFWTSO-UHFFFAOYSA-N Note:

NH O

O F

Reaxys ID 402651 View in Reaxys

77/179 CAS Registry Number: 65610-52-8 Chemical Name: 2-(2-chloro-1-methyl-1H-indol-3-yl)-2-oxoacetyl chloride; (2-chloro-1-methyl-indol-3-yl)-oxo-acetyl chloride Linear Structure Formula: C11H7Cl2NO2 Molecular Formula: C11H7Cl2NO2 Molecular Weight: 256.088 Type of Substance: heterocyclic InChI Key: PKPPWHCQNFHJDL-UHFFFAOYSA-N Note:

N Cl O O

Substance Label (1) Label References 13b

Bergmann et al.; Journal of Heterocyclic Chemistry; vol. 14; (1977); p. 1122,1131, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

123 - 125

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Bergmann et al.; Journal of Heterocyclic Chemistry; vol. 14; (1977); p. 1122,1131, View in Reaxys

Reaxys ID 4867582 View in Reaxys

78/179 CAS Registry Number: 202807-55-4 Chemical Name: (6-chloro-1-methyl-1H-indol-3-yl)-oxo-acetyl chloride Linear Structure Formula: C11H7Cl2NO2 Molecular Formula: C11H7Cl2NO2 Molecular Weight: 256.088 Type of Substance: heterocyclic InChI Key: MOVWHUCLGMYFRJ-UHFFFAOYSA-N Note:

O O

Reaxys ID 4868830 View in Reaxys

79/179 CAS Registry Number: 202807-65-6 Chemical Name: (5-chloro-1-methyl-1H-indol-3-yl)-oxo-acetyl chloride Linear Structure Formula: C11H7Cl2NO2 Molecular Formula: C11H7Cl2NO2 Molecular Weight: 256.088 Type of Substance: heterocyclic InChI Key: QBQCDHCCEVMSHU-UHFFFAOYSA-N Note:

N Cl

O O

Reaxys ID 10439667 View in Reaxys Cl

80/179 Linear Structure Formula: C11H7Cl2NO2 Molecular Formula: C11H7Cl2NO2 Molecular Weight: 256.088 Type of Substance: heterocyclic InChI Key: UPJCXKWLNFGHHO-UHFFFAOYSA-N Note:

O O

Reaxys ID 22921395 View in Reaxys

81/179 O

Linear Structure Formula: C11H7Cl2NO2 Molecular Formula: C11H7Cl2NO2 Molecular Weight: 256.088 InChI Key: KADCOIIQHQFGJE-UHFFFAOYSA-N Note:

Cl NH

Reaxys ID 22819835 View in Reaxys

82/179 Linear Structure Formula: C11H8ClNO2*ClH Molecular Formula: C11H8ClNO2*ClH Molecular Weight: 258.104 InChI Key: GAZCHIARBFHPDJ-UHFFFAOYSA-N Note:

HCl

Cl O

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Reaxys ID 28421844 View in Reaxys

83/179 Linear Structure Formula: C10H4Cl2FNO2 Molecular Formula: C10H4Cl2FNO2 Molecular Weight: 260.052 InChI Key: VMYKMPCURZKZBE-UHFFFAOYSA-N Note:

F NH

Reaxys ID 9918917 View in Reaxys

84/179 CAS Registry Number: 1026482-54-1 Chemical Name: [1-(2-cyanoethyl)indolyl]-3-glyoxylyl chloride Linear Structure Formula: C13H9ClN2O2 Molecular Formula: C13H9ClN2O2 Molecular Weight: 260.68 Type of Substance: heterocyclic InChI Key: PLYBBFODMIYALV-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References 7

Roy, Sudipta; Eastman, Alan; Gribble, Gordon W.; Synthetic Communications; vol. 35; nb. 4; (2005); p. 595 - 601, View in Reaxys

Reaxys ID 15401079 View in Reaxys

85/179 CAS Registry Number: 202807-61-2 Chemical Name: (6-azido-1-methyl-1H-indol-3-yl)-oxo-acetyl chloride Linear Structure Formula: C11H7ClN4O2 Molecular Formula: C11H7ClN4O2 Molecular Weight: 262.655 InChI Key: OYAVWZCFDJYNFB-UHFFFAOYSA-N Note:

Cl N O N

Reaxys ID 4750408 View in Reaxys

86/179 Linear Structure Formula: C13H10ClNO3 Molecular Formula: C13H10ClNO3 Molecular Weight: 263.68 Type of Substance: heterocyclic InChI Key: LFNAGNZWPUAWSW-UHFFFAOYSA-N Note:

NH O

O O

Reaxys ID 8625450 View in Reaxys

87/179 Linear Structure Formula: C14H14ClNO2 Molecular Formula: C14H14ClNO2 Molecular Weight: 263.724 Type of Substance: heterocyclic InChI Key: QRVUZANWWGXDMQ-UHFFFAOYSA-N Note:

O O

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Reaxys ID 22032607 View in Reaxys

88/179

Cl O

Linear Structure Formula: C14H14ClNO2 Molecular Formula: C14H14ClNO2 Molecular Weight: 263.724 InChI Key: LKYVZZFHNXUDOV-UHFFFAOYSA-N Note:

Melting Point (1) 1 of 1

Melting Point [°C]

190 - 191

Solvent (Melting Point)

methanol

German, Nadezhda; Kim, Jin-Sung; Jain, Atul; Dukat, Malgorzata; Pandya, Anshul; Ma, Yilong; Weltzin, Maegan; Schulte, Marvin K.; Glennon, Richard A.; Journal of Medicinal Chemistry; vol. 54; nb. 20; (2011); p. 7259 7267, View in Reaxys Crystal Property Description (1) Colour & Other References Properties brown

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) German, Nadezhda; Kim, Jin-Sung; Jain, Atul; Dukat, Malgorzata; Pandya, Anshul; Ma, Yilong; Weltzin, Maegan; Schulte, Marvin K.; Glennon, Richard A.; Journal of Medicinal Chemistry; vol. 54; nb. 20; (2011); p. 7259 7267, View in Reaxys

Reaxys ID 9775794 View in Reaxys

89/179 CAS Registry Number: 952006-34-7 Linear Structure Formula: C12H8ClNO4 Molecular Formula: C12H8ClNO4 Molecular Weight: 265.653 Type of Substance: heterocyclic InChI Key: FVWNCKFUVIPJAV-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References 5

Shirota, Osamu; Hakamata, Wataru; Goda, Yukihiro; Journal of Natural Products; vol. 66; nb. 6; (2003); p. 885 - 887, View in Reaxys

Crystal Property Description (1) Colour & Other References Properties yellow

Shirota, Osamu; Hakamata, Wataru; Goda, Yukihiro; Journal of Natural Products; vol. 66; nb. 6; (2003); p. 885 - 887, View in Reaxys

Reaxys ID 14008699 View in Reaxys

90/179

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CAS Registry Number: 313337-48-3 Chemical Name: (7-methoxycarbonyl-indol-3-yl)-oxoacetyl chloride Linear Structure Formula: C12H8ClNO4 Molecular Formula: C12H8ClNO4 Molecular Weight: 265.653 InChI Key: LLEKXQUBWGPIRD-UHFFFAOYSA-N Note:

Reaxys ID 19577017 View in Reaxys O

91/179 CAS Registry Number: 1442439-24-8 Linear Structure Formula: C12H8ClNO4 Molecular Formula: C12H8ClNO4 Molecular Weight: 265.653 InChI Key: OCXGHJCJPXWXEP-UHFFFAOYSA-N Note:

O NH

Reaxys ID 21549395 View in Reaxys O

92/179 CAS Registry Number: 1316852-91-1 Linear Structure Formula: C12H8ClNO4 Molecular Formula: C12H8ClNO4 Molecular Weight: 265.653 InChI Key: JGYLURGTICWCCZ-UHFFFAOYSA-N Note:

Cl O

Reaxys ID 22454102 View in Reaxys

93/179 CAS Registry Number: 1370634-96-0 Linear Structure Formula: C12H8ClNO4 Molecular Formula: C12H8ClNO4 Molecular Weight: 265.653 InChI Key: SOWHROOCVMOBPI-UHFFFAOYSA-N Note:

O O NH

Reaxys ID 405994 View in Reaxys

94/179 CAS Registry Number: 52446-40-9 Chemical Name: (5-methoxy-2,7-dimethyl-indol-3-yl)-oxo-acetyl chloride Linear Structure Formula: C13H12ClNO3 Molecular Formula: C13H12ClNO3 Molecular Weight: 265.696 Type of Substance: heterocyclic InChI Key: XSBGIGKKYVWLFK-UHFFFAOYSA-N Note:

NH O

O O

Melting Point (1) 1 of 1

Melting Point [°C]

165 - 168

Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys

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Reaxys ID 7642074 View in Reaxys

95/179 CAS Registry Number: 1027065-12-8 Linear Structure Formula: C13H12ClNO3 Molecular Formula: C13H12ClNO3 Molecular Weight: 265.696 Type of Substance: heterocyclic InChI Key: IQKMTFYCGLLACU-UHFFFAOYSA-N Note:

NH O

O O

Substance Label (1) Label References 2b

Reaxys ID 13676361 View in Reaxys

96/179 Chemical Name: [1-(1-methoxy-ethyl)-1H-indol-3-yl]-oxo-acetyl chloride Linear Structure Formula: C13H12ClNO3 Molecular Formula: C13H12ClNO3 Molecular Weight: 265.696 InChI Key: HEBMFSSLCQLEKH-UHFFFAOYSA-N Note:

O N

Reaxys ID 15401075 View in Reaxys

97/179 CAS Registry Number: 202807-63-4 Chemical Name: (6-ethoxy-1-methyl-1H-indol-3-yl)-oxo-acetyl chloride Linear Structure Formula: C13H12ClNO3 Molecular Formula: C13H12ClNO3 Molecular Weight: 265.696 InChI Key: GHDQKPBSEZCOJO-UHFFFAOYSA-N Note:

O Cl O O N

Reaxys ID 19577015 View in Reaxys

98/179 Linear Structure Formula: C13H12ClNO3 Molecular Formula: C13H12ClNO3 Molecular Weight: 265.696 InChI Key: LAAPQMSCRSFDSA-UHFFFAOYSA-N Note:

Reaxys ID 22637474 View in Reaxys

99/179 CAS Registry Number: 1360151-49-0 Chemical Name: (5-methoxy-1,2-dimethylindol-3-yl)oxoacetyl chloride Linear Structure Formula: C13H12ClNO3 Molecular Formula: C13H12ClNO3 Molecular Weight: 265.696

O N

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InChI Key: LYDWYYSFJKEBQF-UHFFFAOYSA-N Note: Substance Label (1) Label References 6

Shepelenko; Makarova; Karamov; Dubonosov; Podshibakin; Metelitsa; Bren'; Minkin; Chemistry of Heterocyclic Compounds; vol. 50; nb. 7; (2014); p. 932 - 940; Khim. Geterotsikl. Soedin.; vol. 50; nb. 7; (2014); p. 1013 - 1021,9, View in Reaxys

Reaxys ID 23416823 View in Reaxys

100/179 CAS Registry Number: 1428641-83-1 Linear Structure Formula: C13H12ClNO3 Molecular Formula: C13H12ClNO3 Molecular Weight: 265.696 InChI Key: BSJPHYQJOWKOEN-UHFFFAOYSA-N Note:

O NH

Reaxys ID 4874357 View in Reaxys O

101/179 CAS Registry Number: 137467-18-6 Chemical Name: 1-methyl-7-nitroindole-3-glyoxylyl chloride Linear Structure Formula: C11H7ClN2O4 Molecular Formula: C11H7ClN2O4 Molecular Weight: 266.641 Type of Substance: heterocyclic InChI Key: ADURISYFQJCUOT-UHFFFAOYSA-N Note:

O N

O O

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Davis, Peter D.; Hill, Christopher H.; Lawton, Geoffrey; Nixon, John S.; Wilkinson, Sandra E.; et al.; Journal of Medicinal Chemistry; vol. 35; nb. 1; (1992); p. 177 - 184, View in Reaxys

Reaxys ID 4874470 View in Reaxys

102/179

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CAS Registry Number: 202807-43-0 Chemical Name: (1-methyl-6-nitro-1H-indol-3-yl)-oxo-acetyl chloride Linear Structure Formula: C11H7ClN2O4 Molecular Formula: C11H7ClN2O4 Molecular Weight: 266.641 Type of Substance: heterocyclic InChI Key: VTERTDXYBJGLGB-UHFFFAOYSA-N Note:

O N

O O

Reaxys ID 4874702 View in Reaxys

103/179 Linear Structure Formula: C11H7ClN2O4 Molecular Formula: C11H7ClN2O4 Molecular Weight: 266.641 Type of Substance: heterocyclic InChI Key: FVJGJAHQODKWBN-UHFFFAOYSA-N Note:

O O

Reaxys ID 4875384 View in Reaxys

104/179 CAS Registry Number: 125314-83-2 Chemical Name: (1-methyl-5-nitro-1H-indol-3-yl)-oxo-acetyl chloride Linear Structure Formula: C11H7ClN2O4 Molecular Formula: C11H7ClN2O4 Molecular Weight: 266.641 Type of Substance: heterocyclic InChI Key: QQHAARBQMLVNFA-UHFFFAOYSA-N Note:

N O

Melting Point (1) 1 of 1

Melting Point [°C]

161 - 165

Da Settimo, Antonio; Primofiore, Giampaolo; Da Settimo, Federico; Marini, Anna Maria; Novellino, Ettore; Greco, Giovanni; Gesi, Marco; Martini, Claudia; Giannaccini, Gino; Lucacchini, Antonio; Journal of Medicinal Chemistry; vol. 41; nb. 20; (1998); p. 3821 - 3830, View in Reaxys

Reaxys ID 6063173 View in Reaxys

105/179 CAS Registry Number: 61751-67-5 Chemical Name: cloruro dell'acido 5,6-dimetossindol-3-gliossilico; 5,6-dimethoxyindolyl-3-glyoxalyl chloride; 5,6-dimethoxy-3indole-glyoxyl chloride Linear Structure Formula: C12H10ClNO4 Molecular Formula: C12H10ClNO4 Molecular Weight: 267.669 Type of Substance: heterocyclic InChI Key: PCVIPWWVSXLUAY-UHFFFAOYSA-N Note:

O O

Substance Label (2) Label References 12

Sakai, Shin-ichiro; Saito, Naoki; Hirose, Naohiro; Yamanaka, Etsuji; Heterocycles; vol. 17; (1982); p. 99 103, View in Reaxys

Chimenti, F.; Casanova, M. C.; Turini, P.; Sabatini, S.; Farmaco, Edizione Scientifica; vol. 35; nb. 9; (1980); p. 785 - 790, View in Reaxys

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Melting Point (1) 1 of 1

Melting Point [°C]

127 - 128

Solvent (Melting Point)

petroleum ether

Chimenti, F.; Casanova, M. C.; Turini, P.; Sabatini, S.; Farmaco, Edizione Scientifica; vol. 35; nb. 9; (1980); p. 785 - 790, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

Comment (IR Spectroscopy)

3200 - 1775 cm**(-1)

Chimenti, F.; Casanova, M. C.; Turini, P.; Sabatini, S.; Farmaco, Edizione Scientifica; vol. 35; nb. 9; (1980); p. 785 - 790, View in Reaxys

Reaxys ID 6147111 View in Reaxys

106/179 CAS Registry Number: 75909-70-5 Chemical Name: cloruro dell'acido 6,7-dimetossindol-3-gliossilico Linear Structure Formula: C12H10ClNO4 Molecular Formula: C12H10ClNO4 Molecular Weight: 267.669 Type of Substance: heterocyclic InChI Key: NOTSZFJBFGEKTM-UHFFFAOYSA-N Note:

O O

Substance Label (2) Label References 6

Sadanandan, E. V.; Cava, Michael P.; Tetrahedron Letters; vol. 34; nb. 15; (1993); p. 2405 - 2408, View in Reaxys

Chimenti, F.; Casanova, M. C.; Turini, P.; Sabatini, S.; Farmaco, Edizione Scientifica; vol. 35; nb. 9; (1980); p. 785 - 790, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

119 - 120

Solvent (Melting Point)

benzene

Chimenti, F.; Casanova, M. C.; Turini, P.; Sabatini, S.; Farmaco, Edizione Scientifica; vol. 35; nb. 9; (1980); p. 785 - 790, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

Comment (IR Spectroscopy)

3200 - 1780 cm**(-1)

Chimenti, F.; Casanova, M. C.; Turini, P.; Sabatini, S.; Farmaco, Edizione Scientifica; vol. 35; nb. 9; (1980); p. 785 - 790, View in Reaxys

Reaxys ID 19577016 View in Reaxys

107/179

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CAS Registry Number: 587841-94-9 Linear Structure Formula: C12H10ClNO4 Molecular Formula: C12H10ClNO4 Molecular Weight: 267.669 InChI Key: IQDGNEXUUODAES-UHFFFAOYSA-N Note:

NH O

Reaxys ID 20111053 View in Reaxys

108/179 CAS Registry Number: 1388027-77-7 Linear Structure Formula: C12H10ClNO4 Molecular Formula: C12H10ClNO4 Molecular Weight: 267.669 InChI Key: UIDKGHRYYKBTEN-UHFFFAOYSA-N Note:

Reaxys ID 4869554 View in Reaxys

109/179 Linear Structure Formula: C12H10ClNO2S Molecular Formula: C12H10ClNO2S Molecular Weight: 267.736 Type of Substance: heterocyclic InChI Key: SIZWMYNXFVJJAG-UHFFFAOYSA-N Note:

N S O O

Reaxys ID 4870479 View in Reaxys

110/179 Linear Structure Formula: C12H10ClNO2S Molecular Formula: C12H10ClNO2S Molecular Weight: 267.736 Type of Substance: heterocyclic InChI Key: LQBMWHZMYVYUQT-UHFFFAOYSA-N Note:

N S

O O

Reaxys ID 13676767 View in Reaxys

111/179 CAS Registry Number: 202584-18-7 Chemical Name: (1-methyl-6-methylsulfanyl-1H-indol-3-yl)oxo-acetyl chloride Linear Structure Formula: C12H10ClNO2S Molecular Formula: C12H10ClNO2S Molecular Weight: 267.736 InChI Key: OOHMTPJLHLKWLK-UHFFFAOYSA-N Note:

N O S Cl O

Reaxys ID 22677387 View in Reaxys

112/179

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Linear Structure Formula: C12H9ClFNO3 Molecular Formula: C12H9ClFNO3 Molecular Weight: 269.66 InChI Key: DDPOHYUOZHBRQE-UHFFFAOYSA-N Note:

Cl O

Reaxys ID 4466324 View in Reaxys Cl

113/179 Linear Structure Formula: C11H7Cl2NO3 Molecular Formula: C11H7Cl2NO3 Molecular Weight: 272.087 Type of Substance: heterocyclic InChI Key: YMJYGWJYLQYENT-UHFFFAOYSA-N Note:

O O

Reaxys ID 22819834 View in Reaxys

114/179

Linear Structure Formula: C11H8ClNO3*ClH Molecular Formula: C11H8ClNO3*ClH Molecular Weight: 274.103 InChI Key: HVRJCJWUIPKDQO-UHFFFAOYSA-N Note:

HCl

Cl O

Reaxys ID 10447828 View in Reaxys

115/179 N

Linear Structure Formula: C14H11ClN2O2 Molecular Formula: C14H11ClN2O2 Molecular Weight: 274.707 Type of Substance: heterocyclic InChI Key: ZNVHLRRFKTZMNV-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References 16

Roy, Sudipta; Eastman, Alan; Gribble, Gordon W.; Tetrahedron; vol. 62; nb. 33; (2006); p. 7838 - 7845, View in Reaxys

Reaxys ID 9407526 View in Reaxys F

116/179 Linear Structure Formula: C11H5ClF3NO2 Molecular Formula: C11H5ClF3NO2 Molecular Weight: 275.614 Type of Substance: heterocyclic InChI Key: KKUWYENEQGSKJY-UHFFFAOYSA-N Note:

F NH

F O O

Reaxys ID 9407528 View in Reaxys

117/179

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CAS Registry Number: 467461-19-4 Linear Structure Formula: C11H5ClF3NO2 Molecular Formula: C11H5ClF3NO2 Molecular Weight: 275.614 Type of Substance: heterocyclic InChI Key: WGAVFDIEEJJIJR-UHFFFAOYSA-N Note:

NH F O

F O

Reaxys ID 20540749 View in Reaxys

118/179 CAS Registry Number: 1239661-76-7 Linear Structure Formula: C14H10ClNO3 Molecular Formula: C14H10ClNO3 Molecular Weight: 275.691 InChI Key: ZBXJLKAUXZPTLA-UHFFFAOYSA-N Note:

O Cl O NH O

Substance Label (1) Label References intermediate 23

Patent; JANSSEN PHARMACEUTICA NV; SCHOENTJES, Bruno; DESCAMPS, Sophie; AMBLARD, Nathalie, Claudie, Isabelle; WO2010/89327; (2010); (A2) English, View in Reaxys

Reaxys ID 10168750 View in Reaxys Cl

119/179 Linear Structure Formula: C10H4Cl3NO2 Molecular Formula: C10H4Cl3NO2 Molecular Weight: 276.506 Type of Substance: heterocyclic InChI Key: OMDBXPGPQIOHFX-UHFFFAOYSA-N Note:

NH Cl O O

Reaxys ID 3618998 View in Reaxys

120/179 Linear Structure Formula: C13H10ClNO4 Molecular Formula: C13H10ClNO4 Molecular Weight: 279.68 Type of Substance: heterocyclic InChI Key: CYROYWCEGLUTQU-UHFFFAOYSA-N Note:

N O O O

Reaxys ID 23142810 View in Reaxys

121/179 Linear Structure Formula: C13H10ClNO4 Molecular Formula: C13H10ClNO4 Molecular Weight: 279.68 InChI Key: HNLLSNRQVWHFOB-UHFFFAOYSA-N Note:

O Cl

O O O NH

Reaxys ID 19577018 View in Reaxys

122/179

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Linear Structure Formula: C14H14ClNO3 Molecular Formula: C14H14ClNO3 Molecular Weight: 279.723 InChI Key: JUVLKYWAFCGWHX-UHFFFAOYSA-N Note:

NH O

Reaxys ID 9407049 View in Reaxys

123/179 OH

Linear Structure Formula: C13H12ClNO4 Molecular Formula: C13H12ClNO4 Molecular Weight: 281.696 Type of Substance: heterocyclic InChI Key: GSSYEXPLKJEBOK-UHFFFAOYSA-N Note:

O O

Reaxys ID 15291666 View in Reaxys

124/179 CAS Registry Number: 58434-24-5 Chemical Name: 5,6-dimethoxy-2-methyl-indole-3-glyoxyloyl chloride Linear Structure Formula: C13H12ClNO4 Molecular Formula: C13H12ClNO4 Molecular Weight: 281.696 InChI Key: XDKIJVHMXVWURI-UHFFFAOYSA-N Note:

O NH

Reaxys ID 12102474 View in Reaxys

CAS Registry Number: 389628-29-9 Chemical Name: 3-oxoacetyl chloride of 4-fluoro-7-carbomethoxy indole; crude oxo acetyl chloride; crude 3-oxoacetyl chloride of 4-fluoro-7-carbomethoxy indole Linear Structure Formula: C12H7ClFNO4 Molecular Formula: C12H7ClFNO4 Molecular Weight: 283.643 InChI Key: QWKAVBHHHVUBLG-UHFFFAOYSA-N Note:

125/179

NH O

Substance Label (1) Label References 43

Yeung, Kap-Sun; Qiu, Zhilei; Xue, Quifen; Fang, Haiquan; Yang, Zheng; Zadjura, Lisa; D'Arienzo, Celia J.; Eggers, Betsy J.; Riccardi, Keith; Shi, Pei-Yong; Gong, Yi-Fei; Browning, Marc R.; Gao, Qi; Hansel, Steven; Santone, Kenneth; Lin, Ping-Fang; Meanwell, Nicholas A.; Kadow, John F.; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 1; (2013); p. 198 - 202, View in Reaxys

Patent-Specific Data (1) References Patent; Bristol-Myers Squibb Company; US2007/249579; (2007); (A1) English, View in Reaxys

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Reaxys ID 398913 View in Reaxys

126/179 CAS Registry Number: 108061-76-3 Chemical Name: 2-(6-bromo-1H-indol-3-yl)-2-oxoacetyl chloride; indol-3-yl-oxo-acetyl chloride; 6-bromo-indol-3-yl-α-oxoacetyl chloride; 6-bromo-3-indolyl-α-oxoacetyl chloride; 6-bromoindol-3-yl-α-oxoacetyl chloride; (6-bromoindol-3-yl)oxoacetyl chloride; 6-bromoindole-3-glyoxylyl chloride Linear Structure Formula: C10H5O2NClBr Molecular Formula: C10H5BrClNO2 Molecular Weight: 286.512 Type of Substance: heterocyclic InChI Key: AZPMKNMCNCCITK-UHFFFAOYSA-N Note:

O O

Substance Label (12) Label References 42

Patent; THE UNIVERSITY OF BRITISH COLUMBIA; ANDERSEN, Raymond J.; REINER, Neil E.; ZORAGHI, Roya; STRANGMAN, Wendy K.; BOTT, Tina; (98 pag.); WO2016/23106; (2016); (A1) English, View in Reaxys

Zhang, Fengying; Wang, Bin; Prasad, Pritesh; Capon, Robert J.; Jia, Yanxing; Organic Letters; vol. 17; nb. 6; (2015); p. 1529 - 1532, View in Reaxys

Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys; Patent; UNIVERSITE JOSEPH FOURIER; DENIS, Jean-Noël; JOLIVALT, Claude, Marcelle; MAURIN, Max, Maurin, Louis; BURCHAK, Olga, Nikolaevna; WO2013/14104; (2013); (A1) English, View in Reaxys

10b

Guinchard, Xavier; Vallee, Yannick; Denis, Jean-Noel; Journal of Organic Chemistry; vol. 72; nb. 10; (2007); p. 3972 - 3975, View in Reaxys

Higuchi, Kazuhiro; Takei, Ryousuke; Kouko, Takashi; Kawasaki, Tomomi; Synthesis; nb. 5; (2007); p. 669 - 674, View in Reaxys

Kim, Jin-Sung; Padnya, Anshul; Weltzin, Maegan; Edmonds, Brian W.; Schulte, Marvin K.; Glennon, Richard A.; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 17; (2007); p. 4855 - 4860, View in Reaxys

Guinchara, Xavier; Vallee, Yannick; Denis, Jean-Noel; Organic Letters; vol. 9; nb. 19; (2007); p. 3761 3764, View in Reaxys

Kouko, Takashi; Matsumura, Ken; Kawasaki, Tomomi; Tetrahedron; vol. 61; nb. 9; (2005); p. 2309 - 2318, View in Reaxys

Kawasaki, Tomomi; Kouko, Takashi; Totsuka, Hiromi; Hiramatsu, Kei; Tetrahedron Letters; vol. 44; nb. 49; (2003); p. 8849 - 8852, View in Reaxys

Yang, Cai-Guang; Wang, Jun; Tang, Xiao-Xia; Jiang, Biao; Tetrahedron Asymmetry; vol. 13; nb. 4; (2002); p. 383 - 394, View in Reaxys

Jiang, Biao; Yang, Cai-Guang; Wang, Jun; Journal of Organic Chemistry; vol. 67; nb. 4; (2002); p. 1396 1398, View in Reaxys

Jiang; Yang; Wang; Journal of Organic Chemistry; vol. 66; nb. 14; (2001); p. 4865 - 4869, View in Reaxys

Patent-Specific Data (1) Location in Patent References Page/Page column

Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys

Melting Point (2) 1 of 2

Melting Point [°C]

221

Comment (Melting Point)

Decomposition

Jiang; Yang; Wang; Journal of Organic Chemistry; vol. 66; nb. 14; (2001); p. 4865 - 4869, View in Reaxys 2 of 2

Melting Point [°C]

214 - 216

Settimoda et al.; Gazzetta Chimica Italiana; vol. 97; (1967); p. 1304, View in Reaxys Crystal Property Description (3) Colour & Other Location Properties

References

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yellow

Paragraph 0140

Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys

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Page/Page column 24

Patent; UNIVERSITE JOSEPH FOURIER; DENIS, Jean-Noël; JOLIVALT, Claude, Marcelle; MAURIN, Max, Maurin, Louis; BURCHAK, Olga, Nikolaevna; WO2013/14104; (2013); (A1) English, View in Reaxys

yellow

Jiang; Yang; Wang; Journal of Organic Chemistry; vol. 66; nb. 14; (2001); p. 4865 4869, View in Reaxys; Guinchara, Xavier; Vallee, Yannick; Denis, Jean-Noel; Organic Letters; vol. 9; nb. 19; (2007); p. 3761 - 3764, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Jiang; Yang; Wang; Journal of Organic Chemistry; vol. 66; nb. 14; (2001); p. 4865 - 4869, View in Reaxys 2 of 2

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Jiang; Yang; Wang; Journal of Organic Chemistry; vol. 66; nb. 14; (2001); p. 4865 - 4869, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Jiang; Yang; Wang; Journal of Organic Chemistry; vol. 66; nb. 14; (2001); p. 4865 - 4869, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; electron impact (EI)

Jiang; Yang; Wang; Journal of Organic Chemistry; vol. 66; nb. 14; (2001); p. 4865 - 4869, View in Reaxys

Reaxys ID 399068 View in Reaxys

127/179 CAS Registry Number: 63843-81-2 Chemical Name: 2-(5-bromo-1H-indol-3-yl)-2-oxoacetyl chloride; 5-bromo-3-indolylglyoxalyl chloride; (5-bromo-indol-3-yl)oxo-acetyl chloride Linear Structure Formula: C8H5NCOCOClBr Molecular Formula: C10H5BrClNO2 Molecular Weight: 286.512 Type of Substance: heterocyclic InChI Key: WFIILXQRCACCQW-UHFFFAOYSA-N Note:

NH Br

O O

Substance Label (4) Label References

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Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys; Patent; UNIVERSITE JOSEPH FOURIER; DENIS, Jean-Noël; JOLIVALT, Claude, Marcelle; MAURIN, Max, Maurin, Louis; BURCHAK, Olga, Nikolaevna; WO2013/14104; (2013); (A1) English, View in Reaxys

Battaglia, Sandra; Boldrini, Enrico; Da Settimo, Federico; Dondio, Giulio; La Motta, Concettina; Marini, Anna Maria; Primofiore, Giampaolo; European Journal of Medicinal Chemistry; vol. 34; nb. 2; (1999); p. 93 - 105, View in Reaxys; Patent; PROGENICS PHARMACEUTICALS, INC.; WO2009/155527; (2009); (A2) English, View in Reaxys

(I), R=Br, R'=H

Gupta, Leena; Talwar, Archna; Nishi; Palne, Shraddha; Gupta, Suman; Chauhan, Prem M.S.; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 14; (2007); p. 4075 - 4079, View in Reaxys

Meng, Charles Q.; Rakhit, Suman; Lee, David K. H.; Kamboj, Rajender; McCallum, Kirk L.; Mazzocco, Lucy; Dyne, Kerry; Slassi, Abdelmalik; Bioorganic and Medicinal Chemistry Letters; vol. 10; nb. 9; (2000); p. 903 - 905, View in Reaxys

Patent-Specific Data (1) Location in Patent References Page/Page column

Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

212 - 214

Settimoda et al.; Gazzetta Chimica Italiana; vol. 97; (1967); p. 1304, View in Reaxys Crystal Property Description (3) Colour & Other Location Properties

References

yellow

Paragraph 0138

Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys

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Page/Page column 24

Patent; UNIVERSITE JOSEPH FOURIER; DENIS, Jean-Noël; JOLIVALT, Claude, Marcelle; MAURIN, Max, Maurin, Louis; BURCHAK, Olga, Nikolaevna; WO2013/14104; (2013); (A1) English, View in Reaxys

yellow

Patent; PROGENICS PHARMACEUTICALS, INC.; WO2009/155527; (2009); (A2) English, View in Reaxys

Mass Spectrometry (1) Description (Mass References Spectrometry) LCMS (Liquid chromatography mass spectrometry)

Patent; PROGENICS PHARMACEUTICALS, INC.; WO2009/155527; (2009); (A2) English, View in Reaxys

Reaxys ID 5533507 View in Reaxys

128/179 Chemical Name: 2-(7-bromo-1H-indol-3-yl)-2-oxoacetyl chloride Linear Structure Formula: C10H5BrClNO2 Molecular Formula: C10H5BrClNO2 Molecular Weight: 286.512 Type of Substance: heterocyclic InChI Key: CSXUYYVELXAAPF-UHFFFAOYSA-N Note:

Br NH

O O

Substance Label (1) Label References 8k

Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComLocation in Patent References pound

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Paragraph 0148-0149

Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys

Reaxys ID 9395574 View in Reaxys

129/179 CAS Registry Number: 960148-53-2 Chemical Name: 2-(4-bromo-1H-indol-3-yl)-2-oxoacetyl chloride Linear Structure Formula: C10H5BrClNO2 Molecular Formula: C10H5BrClNO2 Molecular Weight: 286.512 Type of Substance: heterocyclic InChI Key: RARGIHXLDQYZKR-UHFFFAOYSA-N Note:

O Br

Substance Label (1) Label References 8j

Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComLocation in Patent References pound prophetic product

Paragraph 0151

Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys

Crystal Property Description (1) Colour & Other Location Properties yellow

References

supporting information

Xu, Xiao-Bo; Liu, Jian; Zhang, Jian-Jian; Wang, Ya-Wen; Peng, Yu; Organic Letters; vol. 15; nb. 3; (2013); p. 550 - 553, View in Reaxys

Reaxys ID 23330578 View in Reaxys

130/179 CAS Registry Number: 1420072-12-3 Chemical Name: 2-(2-bromo-1H-indol-3-yl)-2-oxoacetyl chloride Linear Structure Formula: C10H5BrClNO2 Molecular Formula: C10H5BrClNO2 Molecular Weight: 286.512 InChI Key: CJNWNUKZMBHENY-UHFFFAOYSA-N Note:

NH Br Cl O

Substance Label (1) Label References 8l

Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComLocation in Patent References pound prophetic product

Paragraph 0148-0149

Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys

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Reaxys ID 19740925 View in Reaxys

131/179 CAS Registry Number: 1192478-01-5 Chemical Name: 6-trifluoromethoxyindole glyoxylchloride Linear Structure Formula: C11H5ClF3NO3 Molecular Formula: C11H5ClF3NO3 Molecular Weight: 291.614 InChI Key: VXBLBFSCERUAEU-UHFFFAOYSA-N Note:

Cl O O HN

Substance Label (2) Label References 5

Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/1179; (2010); (A2) English, View in Reaxys

149

Patent; LECTUS THERAPEUTICS LIMITED; WO2009/133387; (2009); (A1) English, View in Reaxys

Reaxys ID 4260660 View in Reaxys

132/179 Linear Structure Formula: C14H12ClNO4 Molecular Formula: C14H12ClNO4 Molecular Weight: 293.707 Type of Substance: heterocyclic InChI Key: OMLRXRXXDPIQPY-UHFFFAOYSA-N Note:

O O

Reaxys ID 5346044 View in Reaxys

133/179 Linear Structure Formula: C14H12ClNO4 Molecular Formula: C14H12ClNO4 Molecular Weight: 293.707 Type of Substance: heterocyclic InChI Key: BGDKVZOOCXSKOB-UHFFFAOYSA-N Note:

O O

Reaxys ID 412372 View in Reaxys

134/179 Chemical Name: 5-Hexyloxyindol-3-glyoxylchlorid Linear Structure Formula: C15H16ClNO3 Molecular Formula: C15H16ClNO3 Molecular Weight: 293.75 Type of Substance: heterocyclic InChI Key: SCYRSUTYSFSOMI-UHFFFAOYSA-N Note:

NH O

O O

Substance Label (1) Label References VIII

Patent; N.V.Phillips Gloeilampenfabrieken; NL6404604; (1964); Chem.Abstr.; vol. 64; nb. 11180b; (1966), View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

125 - 127

Patent; N.V.Phillips Gloeilampenfabrieken; NL6404604; (1964); Chem.Abstr.; vol. 64; nb. 11180b; (1966), View in Reaxys

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Reaxys ID 11041917 View in Reaxys

135/179

Linear Structure Formula: C13H11N2O4Cl Molecular Formula: C13H11ClN2O4 Molecular Weight: 294.694 InChI Key: QWGRCHROUPNNGR-UHFFFAOYSA-N Note:

N O N O

Reaxys ID 9413804 View in Reaxys

136/179 OH

Linear Structure Formula: C14H14ClNO4 Molecular Formula: C14H14ClNO4 Molecular Weight: 295.722 Type of Substance: heterocyclic InChI Key: IDUMYGFNIAXTRG-UHFFFAOYSA-N Note:

O O

Reaxys ID 425147 View in Reaxys

137/179 CAS Registry Number: 97026-81-8 Chemical Name: oxo-(5,6,7-trimethoxy-indol-3-yl)-acetyl chloride; 5,6,7-Trimethoxy-indolyl-3-glyoxylsaeure-chlorid Linear Structure Formula: C13H12ClNO5 Molecular Formula: C13H12ClNO5 Molecular Weight: 297.695 Type of Substance: heterocyclic InChI Key: VKYQGYVLVXFZRQ-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References X

Hardegger; Corrodi; Pharmaceutica Acta Helvetiae; vol. 39; (1964); p. 101,105, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

121

Hardegger; Corrodi; Pharmaceutica Acta Helvetiae; vol. 39; (1964); p. 101,105, View in Reaxys

Reaxys ID 429861 View in Reaxys

138/179 CAS Registry Number: 85503-89-5 Chemical Name: (4,5,6-Trimethoxy-indolyl-3)-glyoxylsaeurechlorid Linear Structure Formula: C13H12ClNO5 Molecular Formula: C13H12ClNO5 Molecular Weight: 297.695 Type of Substance: heterocyclic InChI Key: JLLUZSMOOKHRDT-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References IX

Carlsson,A. et al.; Helvetica Chimica Acta; vol. 46; (1963); p. 1231 - 1235, View in Reaxys

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Reaxys ID 7218448 View in Reaxys

139/179 Linear Structure Formula: C13H12ClNO5 Molecular Formula: C13H12ClNO5 Molecular Weight: 297.695 Type of Substance: heterocyclic InChI Key: BQRDBORKKPVNFC-UHFFFAOYSA-N Note:

O O

Reaxys ID 10450842 View in Reaxys

140/179 Linear Structure Formula: C14H13Cl2NO2 Molecular Formula: C14H13Cl2NO2 Molecular Weight: 298.169 Type of Substance: heterocyclic InChI Key: FKAJREBDQNYTFQ-UHFFFAOYSA-N Note:

NH Cl O

O Cl

Reaxys ID 9265388 View in Reaxys

141/179 Linear Structure Formula: C9H7NCOCOClBr Molecular Formula: C11H7BrClNO2 Molecular Weight: 300.539 Type of Substance: heterocyclic InChI Key: LVZHQOYUUUXYHF-UHFFFAOYSA-N Note:

NH Br

O O

Reaxys ID 11112632 View in Reaxys O Br

142/179 CAS Registry Number: 143137-54-6 Linear Structure Formula: C11H7ClBrNO2 Molecular Formula: C11H7BrClNO2 Molecular Weight: 300.539 InChI Key: XNOQAIXWXINBTD-UHFFFAOYSA-N Note:

O Cl

Reaxys ID 15401006 View in Reaxys

143/179 CAS Registry Number: 202807-59-8 Chemical Name: (6-bromo-1-methyl-1H-indol-3-yl)-oxo-acetyl chloride Linear Structure Formula: C11H7BrClNO2 Molecular Formula: C11H7BrClNO2 Molecular Weight: 300.539 InChI Key: HLJRRGNEADQPHK-UHFFFAOYSA-N Note:

O Cl Br O N

Reaxys ID 415711 View in Reaxys

144/179

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Chemical Name: <1-(2-Diethylamino-ethyl)-indolyl-3>-glyoxylsaeurechlorid; [1-(2-Diethylamino-ethyl)-indolyl-3]-glyoxylsaeurechlorid Linear Structure Formula: C16H19ClN2O2 Molecular Formula: C16H19ClN2O2 Molecular Weight: 306.792 Type of Substance: heterocyclic InChI Key: UPVGBKBKWHRYTQ-UHFFFAOYSA-N Note:

O O

Derivative (1) Comment (Derivative) Hydrochlorid C16H19ClN2O2+ HCl: Prep.: 1-(2Diethylamino-ethyl)-indol, Oxalylchlorid, Dichlorethan, 15grad; orange; zersetzt sich beim Erhitzen auf d. Koflerblock ohne zu schmelzen

References Buzas et al.; Bulletin de la Societe Chimique de France; (1960); p. 644, View in Reaxys

Further Information (1) Description (Fur- References ther Information) Further information

Buzas et al.; Bulletin de la Societe Chimique de France; (1960); p. 644, View in Reaxys

Reaxys ID 5347916 View in Reaxys

145/179 Linear Structure Formula: C15H14ClNO4 Molecular Formula: C15H14ClNO4 Molecular Weight: 307.733 Type of Substance: heterocyclic InChI Key: YRPYDRYVKUVEQS-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References 2 (tab. run 8)

Bit, Rino A.; Crackett, Peter H.; Harris, William; Hill, Christopher H.; Tetrahedron Letters; vol. 34; nb. 35; (1993); p. 5623 - 5626, View in Reaxys

Reaxys ID 8272313 View in Reaxys

146/179 Linear Structure Formula: C12H5Cl2NO5 Molecular Formula: C12H5Cl2NO5 Molecular Weight: 314.081 Type of Substance: heterocyclic InChI Key: UKWUVOUPQVVPOU-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References 9

Sogawa, Kazuyo; Hashimoto, Kimiko; Shirahama, Haruhisa; Heterocycles; vol. 50; nb. 2; (1999); p. 657 660, View in Reaxys

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Reaxys ID 14389483 View in Reaxys

147/179 Cl

Linear Structure Formula: C12H9BrClNO2 Molecular Formula: C12H9BrClNO2 Molecular Weight: 314.566 InChI Key: UDSXARDZKBZOIW-UHFFFAOYSA-N Note:

Br NH

Reaxys ID 13480956 View in Reaxys

148/179 CAS Registry Number: 81880-76-4 Chemical Name: 5-[[(methylsulphonyl)amino]methyl]-αoxo-1H-indole-3-acetyl chloride; 5-[[(methylsulphonyl)amino]methyl]-α-oxo-1H-indole-3-acetyl chloride Linear Structure Formula: C12H11ClN2O4S Molecular Formula: C12H11ClN2O4S Molecular Weight: 314.749 InChI Key: JEICHPBIQXNCHQ-UHFFFAOYSA-N Note:

HN H N

O S

O O Cl

Melting Point (1) 1 of 1

Melting Point [°C]

135

Patent; Glaxo Group Limited; US4636521; (1987); (A1) English, View in Reaxys

Reaxys ID 433875 View in Reaxys

149/179 CAS Registry Number: 50627-45-7 Linear Structure Formula: C13H11Cl2NO4 Molecular Formula: C13H11Cl2NO4 Molecular Weight: 316.141 Type of Substance: heterocyclic InChI Key: NGQYPQKOMLKFSH-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References X=COCOCl

Kishi; Nakatsuka; Fukuyama; Havel; Journal of the American Chemical Society; vol. 95; nb. 19; (1973); p. 6493 - 6495, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

140

Kishi; Nakatsuka; Fukuyama; Havel; Journal of the American Chemical Society; vol. 95; nb. 19; (1973); p. 6493 6495, View in Reaxys

Reaxys ID 4474108 View in Reaxys

150/179 Linear Structure Formula: C11H7BrClNO3 Molecular Formula: C11H7BrClNO3 Molecular Weight: 316.538 Type of Substance: heterocyclic InChI Key: CVRRCQBLYBDRBD-UHFFFAOYSA-N Note:

Br NH

O O

Substance Label (2) Label References

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S3.16

Patent; YALE UNIVERSITY; SPIEGAL, David; PARKER, Christopher; WO2013/162757; (2013); (A1) English, View in Reaxys

Kim, Phieo Ta; Guillard, Roger; Samreth, Soth; Sornay, Roland; Journal of Heterocyclic Chemistry; vol. 18; (1981); p. 1373 - 1377, View in Reaxys

Reaxys ID 21751174 View in Reaxys

151/179 Cl

Linear Structure Formula: C11H7BrClNO3 Molecular Formula: C11H7BrClNO3 Molecular Weight: 316.538 InChI Key: BHQKZQREHQPQJW-UHFFFAOYSA-N Note:

NH O

Reaxys ID 10168035 View in Reaxys

152/179 Linear Structure Formula: C10H4BrCl2NO2 Molecular Formula: C10H4BrCl2NO2 Molecular Weight: 320.957 Type of Substance: heterocyclic InChI Key: WLRWNHMEMLVHPM-UHFFFAOYSA-N Note:

NH Cl Br

O O

Reaxys ID 5348348 View in Reaxys

153/179 O

Linear Structure Formula: C16H16ClNO4 Molecular Formula: C16H16ClNO4 Molecular Weight: 321.76 Type of Substance: heterocyclic InChI Key: FDUUWRSNKIXKRG-UHFFFAOYSA-N Note:

O O

Reaxys ID 5585886 View in Reaxys

154/179 Linear Structure Formula: C16H16ClNO4 Molecular Formula: C16H16ClNO4 Molecular Weight: 321.76 Type of Substance: heterocyclic InChI Key: DJDUYXGCUAUOTB-UHFFFAOYSA-N Note:

O O

Reaxys ID 7304465 View in Reaxys

155/179

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Linear Structure Formula: C16H16ClNO4 Molecular Formula: C16H16ClNO4 Molecular Weight: 321.76 Type of Substance: heterocyclic InChI Key: LMCUDAIDPOOLOS-UHFFFAOYSA-N Note:

O O

Reaxys ID 23170044 View in Reaxys

156/179 Linear Structure Formula: C15H15ClN2O4 Molecular Formula: C15H15ClN2O4 Molecular Weight: 322.748 InChI Key: FHZQQQNHAQYNHB-UHFFFAOYSA-N Note:

HN NH

Reaxys ID 23170045 View in Reaxys

157/179 Linear Structure Formula: C15H15ClN2O4 Molecular Formula: C15H15ClN2O4 Molecular Weight: 322.748 InChI Key: CKLKKSHQLWOJIP-UHFFFAOYSA-N Note:

HN O

Reaxys ID 11041921 View in Reaxys O

158/179

Linear Structure Formula: C13H11NBrClO2 Molecular Formula: C13H11BrClNO2 Molecular Weight: 328.593 InChI Key: ZGWIIYUIUIPPBS-UHFFFAOYSA-N Note:

Reaxys ID 14389489 View in Reaxys Br

159/179 Linear Structure Formula: C13H11BrClNO2 Molecular Formula: C13H11BrClNO2 Molecular Weight: 328.593 InChI Key: NPIHMCQMEHJRMW-UHFFFAOYSA-N Note:

O Cl O NH

Reaxys ID 27133312 View in Reaxys

160/179

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CAS Registry Number: 1617530-95-6 Linear Structure Formula: C13H13ClNO5P Molecular Formula: C13H13ClNO5P Molecular Weight: 329.677 InChI Key: SDBRWABASKVIJK-UHFFFAOYSA-N Note:

O Cl

O O

Substance Label (2) Label References 13a

McNulty, James; Keskar, Kunal; Jenkins, Hilary A.; Werstiuk, Nick H.; Bordn, Claudia; Yolken, Robert; Jones-Brando, Lorraine; Organic and Biomolecular Chemistry; vol. 13; nb. 39; (2015); p. 10015 - 10024, View in Reaxys

McNulty; Keskar; Bordon; Yolken; Jones-Brando; Chemical Communications; vol. 50; nb. 64; (2014); p. 8904 - 8907, View in Reaxys

Reaxys ID 13681919 View in Reaxys

161/179 Chemical Name: (6-trifluoroacetylamino-1-methyl-1H-indol-3yl)-oxo-acetyl chloride Linear Structure Formula: C13H8ClF3N2O3 Molecular Formula: C13H8ClF3N2O3 Molecular Weight: 332.666 InChI Key: KZLVMCGDHNDZEL-UHFFFAOYSA-N Note:

N O NH

F F

Cl O

Reaxys ID 20155423 View in Reaxys

162/179 Chemical Name: 2-(5-iodo-1H-indol-3-yl)-2-oxoacetyl chloride Linear Structure Formula: C10H5ClINO2 Molecular Formula: C10H5ClINO2 Molecular Weight: 333.513 InChI Key: SNNFNZRIESVIFE-UHFFFAOYSA-N Note:

NH I

O O

Substance Label (1) Label References 8h

Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComLocation in Patent References pound prophetic product

Paragraph 0148-0149

Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys

Reaxys ID 23330577 View in Reaxys

163/179 CAS Registry Number: 1420072-11-2 Chemical Name: 2-(6-iodo-1H-indol-3-yl)-2-oxoacetyl chloride Linear Structure Formula: C10H5ClINO2 Molecular Formula: C10H5ClINO2 Molecular Weight: 333.513 InChI Key: XRDBSFHZTMINHY-UHFFFAOYSA-N Note:

Cl O

Substance Label (1)

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Label

References

Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComLocation in Patent References pound prophetic product

Paragraph 0148-0149

Patent; Université Joseph Fourier; Denis, Jean-Noël; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Burchak, Olga, Nikolaevna; EP2548865; (2013); (A1) English, View in Reaxys

Reaxys ID 5350650 View in Reaxys

164/179 Linear Structure Formula: C17H18ClNO4 Molecular Formula: C17H18ClNO4 Molecular Weight: 335.787 Type of Substance: heterocyclic InChI Key: UPHHDCYTRINBHW-UHFFFAOYSA-N Note:

O O

Reaxys ID 15401029 View in Reaxys

165/179 CAS Registry Number: 202807-60-1 Chemical Name: (6-iodo-1-methyl-1H-indol-3-yl)-oxo-acetyl chloride Linear Structure Formula: C11H7ClINO2 Molecular Formula: C11H7ClINO2 Molecular Weight: 347.54 InChI Key: DMGKWTXFINJXSA-UHFFFAOYSA-N Note:

O Cl I O N

Reaxys ID 10467288 View in Reaxys

166/179 Linear Structure Formula: C17H18ClNO5 Molecular Formula: C17H18ClNO5 Molecular Weight: 351.787 Type of Substance: heterocyclic InChI Key: YASZUZLTAUPNLB-UHFFFAOYSA-N Note:

O O

Reaxys ID 22741768 View in Reaxys

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CAS Registry Number: 1378020-92-8 Chemical Name: 2-(5-bromo-1-pentyl-1H-indol-3-yl)-2-oxoacetyl chloride Linear Structure Formula: C15H15BrClNO2 Molecular Formula: C15H15BrClNO2 Molecular Weight: 356.647 InChI Key: LGEUTWLTQOQROB-UHFFFAOYSA-N Note:

Br N

Reaxys ID 19668788 View in Reaxys

168/179 Linear Structure Formula: C19H26ClNO2Si Molecular Formula: C19H26ClNO2Si Molecular Weight: 363.959 InChI Key: DCJLWOYORWYWDH-UHFFFAOYSA-N Note:

N Si

Reaxys ID 11258979 View in Reaxys

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Linear Structure Formula: C19H23ClN2O4 Molecular Formula: C19H23ClN2O4 Molecular Weight: 378.856 InChI Key: ROEYSIMSKWRWDV-UHFFFAOYSA-N Note:

Cl O N

N O

Reaxys ID 9424876 View in Reaxys

170/179 Linear Structure Formula: C19H26ClNO3Si Molecular Formula: C19H26ClNO3Si Molecular Weight: 379.959 Type of Substance: heterocyclic InChI Key: UGFLBZYXRHUBMV-UHFFFAOYSA-N Note:

Si O

O O

Reaxys ID 9429492 View in Reaxys

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Linear Structure Formula: C19H26ClNO3Si Molecular Formula: C19H26ClNO3Si Molecular Weight: 379.959 Type of Substance: heterocyclic InChI Key: FQBOLOGCDNHEBK-UHFFFAOYSA-N Note:

Si O

O O

Reaxys ID 9722971 View in Reaxys

172/179 Linear Structure Formula: C20H28ClNO3Si Molecular Formula: C20H28ClNO3Si Molecular Weight: 393.986 Type of Substance: heterocyclic InChI Key: CQAWVQABIOJAEQ-UHFFFAOYSA-N Note:

O O

Reaxys ID 7037470 View in Reaxys

173/179 CAS Registry Number: 158920-13-9 Chemical Name: <(6,7-Dibromo-4-methoxy)indol-3-yl>-α-oxoacetyl chloride; [(6,7-Dibromo-4-methoxy)indol-3-yl]-α-oxoacetyl chloride Linear Structure Formula: C11H6Br2ClNO3 Molecular Formula: C11H6Br2ClNO3 Molecular Weight: 395.435 Type of Substance: heterocyclic InChI Key: MAYPJINVAIFJFM-UHFFFAOYSA-N Note:

Br Br

O O

Substance Label (1) Label References 14a

Jiang; Smallheer; Amaral-Ly; Wuonola; Journal of Organic Chemistry; vol. 59; nb. 22; (1994); p. 6823 6827, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

264.7

Comment (Melting Point)

Decomposition

Jiang; Smallheer; Amaral-Ly; Wuonola; Journal of Organic Chemistry; vol. 59; nb. 22; (1994); p. 6823 - 6827, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Jiang; Smallheer; Amaral-Ly; Wuonola; Journal of Organic Chemistry; vol. 59; nb. 22; (1994); p. 6823 - 6827, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

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Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

3165 - 1608 cm**(-1)

Jiang; Smallheer; Amaral-Ly; Wuonola; Journal of Organic Chemistry; vol. 59; nb. 22; (1994); p. 6823 - 6827, View in Reaxys

Reaxys ID 7727966 View in Reaxys

174/179 Linear Structure Formula: C18H18ClNO7 Molecular Formula: C18H18ClNO7 Molecular Weight: 395.796 Type of Substance: heterocyclic InChI Key: KLWWHNMULXKIKC-MRXNPFEDSA-N Note:

O O O O

O N

O O

Reaxys ID 11306093 View in Reaxys

175/179 Linear Structure Formula: C20H28ClNO4Si Molecular Formula: C20H28ClNO4Si Molecular Weight: 409.985 InChI Key: ZHCDWJWKXMZEFA-UHFFFAOYSA-N Note:

O Cl O N

Reaxys ID 7665928 View in Reaxys

176/179 CAS Registry Number: 1028309-58-1 Linear Structure Formula: C22H28ClNO5 Molecular Formula: C22H28ClNO5 Molecular Weight: 421.921 Type of Substance: heterocyclic InChI Key: MRJLDYOZOKIBLF-UHFFFAOYSA-N Note:

O O

Reaxys ID 10502413 View in Reaxys

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Linear Structure Formula: C30H46ClNO3 Molecular Formula: C30H46ClNO3 Molecular Weight: 504.153 Type of Substance: heterocyclic InChI Key: MVDDYBNRSWSDFR-UHFFFAOYSA-N Note:

N O

O O

Reaxys ID 15402557 View in Reaxys

178/179 Chemical Name: (1,6-dimethyl-1H-indol-3-yl)-oxo-acetyl chloride 2-(1,5-dimethyl-1H-indol-3-yl)-acetimidic acid isopropyl ester hydrochloride Linear Structure Formula: C12H10ClNO2*C15H20N2O*ClH Molecular Formula: C12H10ClNO2*C15H20N2O*ClH Molecular Weight: 516.467 InChI Key: NHIPEMRMYAODNZ-UHFFFAOYSA-N Note:

O Cl O N

O HN N HCl

Reaxys ID 15402598 View in Reaxys

179/179 Chemical Name: (6-cyano-1-methyl-1H-indol-3-yl)-oxo-acetyl chloride 2-(5-methoxy-1-methyl-1H-indol-3-yl)-acetimidic acid isopropyl ester hydrochloride Linear Structure Formula: C12H7ClN2O2*C15H20N2O2*ClH Molecular Formula: C12H7ClN2O2*C15H20N2O2*ClH Molecular Weight: 543.45 InChI Key: JGHNRANRTUFQAR-UHFFFAOYSA-N Note:

O Cl N O N

O O HN N HCl

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