1-(8-Bromofuro[2,3-f][1]benzofuran-4-yl)propan-2-amine [Bromo-DragonFLY]

Page 1

Reaxys

PubChem

eMolecules

Reactions (21)

Yield

Substances (4)

Conditions

Citations (3)

References

1

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Rx-ID: 31058497 Find similar reactions

in ethanol; water

0.166667 h; Reflux;

2

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Smith, Graham; Cotton, Marcus S.; Wermuth, Urs D.; Boyd, Sue E.

Acta Crystallographica Section C: Crystal Structure Communications, 2010 , vol. 66, # 5 p. o252-o255 Title/Abstract Full Text View citing articles Show Details


Synthesize Find similar With sodium hydroxide in methanol

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Rx-ID: 8847905 Find similar reactions

Chambers; Kurrasch-Orbaugh; Parker; Nichols

Journal of Medicinal Chemistry, 2001 , vol. 44, # 6 p. 1003 - 1010 Title/Abstract Full Text View citing articles Show Details

3

Synthesize Find similar With sodium hydroxide in methanol

Synthesize Find similar

Rx-ID: 8847906 Find similar reactions

Chambers; Kurrasch-Orbaugh; Parker; Nichols

Journal of Medicinal Chemistry, 2001 , vol. 44, # 6 p. 1003 - 1010 Title/Abstract Full Text View citing articles Show Details

4

Synthesize Find similar Multi-step reaction with 7 steps 1: 91 percent / Br2; ZnCl2 / acetic acid 2: 79 percent / Mg; EtMgBr / tetrahydrofuran / 3 h / Heating 3: AlCl3 / CH2Cl2 / 16 h 4: 94 percent / TFA; Et3SiH / 6 h / Heating 5: 82 percent / Br2 / acetic acid / 4.5 h / 20 °C 6: 64 percent / DDQ / dioxane / 24 h / Heating 7: aq. 5 N NaOH / methanol View Scheme

5

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Rx-ID: 15299180 Find similar reactions

Chambers; Kurrasch-Orbaugh; Parker; Nichols

Journal of Medicinal Chemistry, 2001 , vol. 44, # 6 p. 1003 - 1010 Title/Abstract Full Text View citing articles Show Details


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6

Multi-step reaction with 7 steps 1: 91 percent / Br2; ZnCl2 / acetic acid 2: 79 percent / Mg; EtMgBr / tetrahydrofuran / 3 h / Heating 3: AlCl3 / CH2Cl2 / 16 h 4: 92 percent / TFA; Et3SiH / 6 h / Heating 5: 79 percent / Br2 / acetic acid / 4.5 h / 20 °C 6: 68 percent / DDQ / dioxane / 24 h / Heating 7: aq. 5 N NaOH / methanol View Scheme

Multi-step reaction with 8 steps 1: 88 percent / SOCl2; pyridine / 20 °C 2: 91 percent / Br2; ZnCl2 / acetic acid 3: 79 percent / Mg; EtMgBr / tetrahydrofuran / 3 h / Heating 4: AlCl3 / CH2Cl2 / 16 h 5: 94 percent / TFA; Et3SiH / 6 h / Heating 6: 82 percent / Br2 / acetic acid / 4.5 h / 20 °C 7: 64 percent / DDQ / dioxane / 24 h / Heating 8: aq. 5 N NaOH / methanol View Scheme

Chambers; Kurrasch-Orbaugh; Parker; Nichols

Journal of Medicinal Chemistry, 2001 , vol. 44, # 6 p. 1003 - 1010 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 15306639 Find similar reactions

Chambers; Kurrasch-Orbaugh; Parker; Nichols

Journal of Medicinal Chemistry, 2001 , vol. 44, # 6 p. 1003 - 1010 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 15299181 Find similar reactions

Synthesize Find similar

7

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Multi-step reaction with 8 steps 1: 88 percent / SOCl2; pyridine / 20 °C 2: 91 percent / Br2; ZnCl2 / acetic acid 3: 79 percent / Mg; EtMgBr / tetrahydrofuran / 3 h / Heating 4: AlCl3 / CH2Cl2 / 16 h 5: 92 percent / TFA; Et3SiH / 6 h / Heating 6: 79 percent / Br2 / acetic acid / 4.5 h / 20 °C 7: 68 percent / DDQ / dioxane / 24 h / Heating 8: aq. 5 N NaOH / methanol

Synthesize Find similar

Rx-ID: 15306640 Find similar reactions

Chambers; Kurrasch-Orbaugh; Parker; Nichols

Journal of Medicinal Chemistry, 2001 , vol. 44, # 6 p. 1003 - 1010 Title/Abstract Full Text View citing articles Show Details


View Scheme

8

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9

Multi-step reaction with 5 steps 1: AlCl3 / CH2Cl2 / 16 h 2: 94 percent / TFA; Et3SiH / 6 h / Heating 3: 82 percent / Br2 / acetic acid / 4.5 h / 20 °C 4: 64 percent / DDQ / dioxane / 24 h / Heating 5: aq. 5 N NaOH / methanol View Scheme

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Rx-ID: 15307123 Find similar reactions

Chambers; Kurrasch-Orbaugh; Parker; Nichols

Journal of Medicinal Chemistry, 2001 , vol. 44, # 6 p. 1003 - 1010 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Multi-step reaction with 5 steps 1: AlCl3 / CH2Cl2 / 16 h 2: 92 percent / TFA; Et3SiH / 6 h / Heating 3: 79 percent / Br2 / acetic acid / 4.5 h / 20 °C 4: 68 percent / DDQ / dioxane / 24 h / Heating 5: aq. 5 N NaOH / methanol View Scheme

Synthesize Find similar

Rx-ID: 15307124 Find similar reactions

Chambers; Kurrasch-Orbaugh; Parker; Nichols

Journal of Medicinal Chemistry, 2001 , vol. 44, # 6 p. 1003 - 1010 Title/Abstract Full Text View citing articles Show Details

10

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Synthesize Find similar

Rx-ID: 15310221 Find similar reactions


Multi-step reaction with 6 steps 1: 79 percent / Mg; EtMgBr / tetrahydrofuran / 3 h / Heating 2: AlCl3 / CH2Cl2 / 16 h 3: 94 percent / TFA; Et3SiH / 6 h / Heating 4: 82 percent / Br2 / acetic acid / 4.5 h / 20 °C 5: 64 percent / DDQ / dioxane / 24 h / Heating 6: aq. 5 N NaOH / methanol View Scheme

Chambers; Kurrasch-Orbaugh; Parker; Nichols

Journal of Medicinal Chemistry, 2001 , vol. 44, # 6 p. 1003 - 1010 Title/Abstract Full Text View citing articles Show Details

11

Synthesize Find similar

Multi-step reaction with 6 steps 1: 79 percent / Mg; EtMgBr / tetrahydrofuran / 3 h / Heating 2: AlCl3 / CH2Cl2 / 16 h 3: 92 percent / TFA; Et3SiH / 6 h / Heating 4: 79 percent / Br2 / acetic acid / 4.5 h / 20 °C 5: 68 percent / DDQ / dioxane / 24 h / Heating 6: aq. 5 N NaOH / methanol View Scheme

Synthesize Find similar

Rx-ID: 15310222 Find similar reactions

Chambers; Kurrasch-Orbaugh; Parker; Nichols

Journal of Medicinal Chemistry, 2001 , vol. 44, # 6 p. 1003 - 1010 Title/Abstract Full Text View citing articles Show Details

12

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13

Multi-step reaction with 3 steps 1: 82 percent / Br2 / acetic acid / 4.5 h / 20 °C 2: 64 percent / DDQ / dioxane / 24 h / Heating 3: aq. 5 N NaOH / methanol View Scheme

Synthesize Find similar

Rx-ID: 15325685 Find similar reactions

Chambers; Kurrasch-Orbaugh; Parker; Nichols

Journal of Medicinal Chemistry, 2001 , vol. 44, # 6 p. 1003 - 1010 Title/Abstract Full Text View citing articles Show Details


Synthesize Find similar

Multi-step reaction with 3 steps 1: 79 percent / Br2 / acetic acid / 4.5 h / 20 °C 2: 68 percent / DDQ / dioxane / 24 h / Heating 3: aq. 5 N NaOH / methanol View Scheme

Synthesize Find similar

Rx-ID: 15325693 Find similar reactions

Chambers; Kurrasch-Orbaugh; Parker; Nichols

Journal of Medicinal Chemistry, 2001 , vol. 44, # 6 p. 1003 - 1010 Title/Abstract Full Text View citing articles Show Details

14

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Multi-step reaction with 4 steps 1: 94 percent / TFA; Et3SiH / 6 h / Heating 2: 82 percent / Br2 / acetic acid / 4.5 h / 20 °C 3: 64 percent / DDQ / dioxane / 24 h / Heating 4: aq. 5 N NaOH / methanol View Scheme

Synthesize Find similar

Rx-ID: 15326442 Find similar reactions

Chambers; Kurrasch-Orbaugh; Parker; Nichols

Journal of Medicinal Chemistry, 2001 , vol. 44, # 6 p. 1003 - 1010 Title/Abstract Full Text View citing articles Show Details

15

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Multi-step reaction with 4 steps 1: 92 percent / TFA; Et3SiH / 6 h / Heating 2: 79 percent / Br2 / acetic acid / 4.5 h / 20 °C 3: 68 percent / DDQ / dioxane / 24 h / Heating 4: aq. 5 N NaOH / methanol View Scheme

Synthesize Find similar

Rx-ID: 15326453 Find similar reactions

Chambers; Kurrasch-Orbaugh; Parker; Nichols

Journal of Medicinal Chemistry, 2001 , vol. 44, # 6 p. 1003 - 1010 Title/Abstract Full Text View citing articles Show Details


16

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Multi-step reaction with 2 steps 1: 64 percent / DDQ / dioxane / 24 h / Heating 2: aq. 5 N NaOH / methanol View Scheme

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Rx-ID: 15327442 Find similar reactions

Chambers; Kurrasch-Orbaugh; Parker; Nichols

Journal of Medicinal Chemistry, 2001 , vol. 44, # 6 p. 1003 - 1010 Title/Abstract Full Text View citing articles Show Details

17

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Multi-step reaction with 2 steps 1: 68 percent / DDQ / dioxane / 24 h / Heating 2: aq. 5 N NaOH / methanol View Scheme

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Rx-ID: 15327446 Find similar reactions

Chambers; Kurrasch-Orbaugh; Parker; Nichols

Journal of Medicinal Chemistry, 2001 , vol. 44, # 6 p. 1003 - 1010 Title/Abstract Full Text View citing articles Show Details

18

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With sodium hydroxide in methanol

12 h; Ambient temperature;

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Rx-ID: 5121917 Find similar reactions

Parker, Matthew A.; Marona-Lewicka, Danuta; Lucaites, Virginia L.; Nelson, David L.; Nichols, David E.

Journal of Medicinal Chemistry, 1998 , vol. 41, # 26 p. 5148 - 5149 Title/Abstract Full Text View citing articles Show Details


19

Synthesize Find similar Multi-step reaction with 4 steps 1: 87 percent / Et3N / CH2Cl2 / 2 h / 0 - 20 °C 2: 71 percent / Br2, AcOH / 5 h / 15 - 20 °C 3: 89 percent / DDQ / toluene / 10.5 h / Heating 4: aq. NaOH / methanol / 12 h / Ambient temperature View Scheme

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Rx-ID: 16445360 Find similar reactions

Parker, Matthew A.; Marona-Lewicka, Danuta; Lucaites, Virginia L.; Nelson, David L.; Nichols, David E.

Journal of Medicinal Chemistry, 1998 , vol. 41, # 26 p. 5148 - 5149 Title/Abstract Full Text View citing articles Show Details

20

Synthesize Find similar Multi-step reaction with 3 steps 1: 71 percent / Br2, AcOH / 5 h / 15 - 20 °C 2: 89 percent / DDQ / toluene / 10.5 h / Heating 3: aq. NaOH / methanol / 12 h / Ambient temperature View Scheme

Synthesize Find similar

Rx-ID: 16455630 Find similar reactions

Parker, Matthew A.; Marona-Lewicka, Danuta; Lucaites, Virginia L.; Nelson, David L.; Nichols, David E.

Journal of Medicinal Chemistry, 1998 , vol. 41, # 26 p. 5148 - 5149 Title/Abstract Full Text View citing articles Show Details

21

Synthesize Find similar Multi-step reaction with 2 steps 1: 89 percent / DDQ / toluene / 10.5 h / Heating 2: aq. NaOH / methanol / 12 h / Ambient temperature View Scheme

Synthesize Find similar

Rx-ID: 16457110 Find similar reactions

Parker, Matthew A.; Marona-Lewicka, Danuta; Lucaites, Virginia L.; Nelson, David L.; Nichols, David E.

Journal of Medicinal Chemistry, 1998 , vol. 41, # 26 p. 5148 - 5149 Title/Abstract Full Text View citing articles Show Details


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