Triethylamine → N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-methyl-2-phenylfuran-3-carboxamide

HRID 1918770노트

반응식

HRID 1918770 반응식
C(N(CC)CC)C.Cl.[Cl:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[CH2:19][CH2:20][NH2:21].[CH3:22][C:23]1[O:27][C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:25]([C:34](Cl)=[O:35])[CH:24]=1>ClCCl>[Cl:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[CH2:19][CH2:20][NH:21][C:34]([C:25]1[CH:24]=[C:23]([CH3:22])[O:27][C:26]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:35]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochlorideHCID 152697375-Methyl-2-phenylfuran-3-carbonyl chloride

생성물 1

HCID 66831979N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-methyl-2-phenylfuran-3-carboxamide수율 86.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Triethylamine (0.128 mL; 0.886 mmol) was added to a mixture of 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.082 g; 0.354 mmol) and 5-methyl-2-phenylfuran-3-carbonyl chloride (0.082 g; 0.372 mmol) in dichloromethane (7 mL) at room temperature. The reaction mixture was stirred at room temperature for 20 minutes and washed with water. The organic layer was concentrated under reduced pressure and the crude material was purified by flash chromatography on silica gel (eluent 2 to 10% ethyl acetate in dichloromethane) to afford 0.116 g (86%) of N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-methyl-2-phenylfuran-3-carboxamide as a solid.

후처리

  1. washwashed with water
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe crude material was purified by flash chromatography on silica gel (eluent 2 to 10% ethyl acetate in dichloromethane)

출처 및 근거

ORD 기록
ord-720746514e91467b97f1cc63181e496e
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618138B2

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