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

反応式

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]

参加物

反応物 4

HCID 6228Dimethylformamide

HCID 14798Sodium Hydroxide

HCID 4437323-Buten-1-amine

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

生成物 1

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

反応条件

温度: 80 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード: ord-d9649af933174d8c815aa61f0a24261e
出典データセット: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US06503907B2

反応ノート

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