Dimethylformamide → Allyl-{4-[1-(4-chloro-phenyl)-6-fluoro-1H-indol-5-yloxy]-butyl}-methyl-amine

HRID 1633706노트

반응식

Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[F:16])[N:12]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[CH:11]=[CH:10]2.[CH2:24]([CH2:27][NH2:28])[CH:25]=C.[OH-].[Na+].[CH3:31]N(C=O)C>>[CH2:27]([N:28]([CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[F:16])[N:12]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[CH:11]=[CH:10]2)[CH3:31])[CH:24]=[CH2:25]

참가 물질

반응물 4

HCID 6228Dimethylformamide

HCID 14798Sodium Hydroxide

HCID 4437323-Buten-1-amine

HCID 186794855-(4-Bromo-butoxy)-1-(4-chloro-phenyl)-6-fluoro-1H-indole

생성물 1

HCID 18679530Allyl-{4-[1-(4-chloro-phenyl)-6-fluoro-1H-indol-5-yloxy]-butyl}-methyl-amine수율 85%

반응 조건

온도: 80 °C

실험 절차

30 mg (0.076 mmol) 5-(4-Bromo-butoxy)-1-(4-chloro-phenyl)-6-fluoro-1H-indole in 0.25 ml DMF were treated with 75 μl of N-Allylmethylamine and stirred at 80° C. during 1 h. The mixture was treated with 0.5M aqueous NaOH and extracted three times with Et2O. Drying of the combined organic layers with Na2SO4, evaporation of the solvent and column chromatography on silica gel with hexane/EtOAc 1:1 gave 25 mg (85%) Allyl-{4-[1-(4-chloro-phenyl)-6-fluoro-1H-indol-5-yloxy]-butyl}-methyl-amine as a light yellow oil, MS: 387 (MH+, 1Cl).

후처리

extractionextracted three times with Et2O
dry with materialDrying of the combined organic layers with Na2SO4, evaporation of the solvent and column chromatography on silica gel with hexane/EtOAc 1:1

출처 및 근거

ORD 기록: ord-d9649af933174d8c815aa61f0a24261e
출처 데이터셋: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US06503907B2

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