Ammonia → 5-Benzyloxy-6-methyl-1H-indole-2-carboxylic acid methyl ester

HRID 73330노트

반응식

HRID 73330 반응식
[CH3:1][O:2][C:3](=[O:33])/[C:4](/[NH:22]C(OCC1C=CC=CC=1)=O)=[CH:5]/[C:6]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9]([CH3:20])=[CH:8][C:7]=1Br.C([O-])(=O)C.[Cs+].N>CS(C)=O.[Cu]I>[CH3:1][O:2][C:3]([C:4]1[NH:22][C:7]2[C:6]([CH:5]=1)=[CH:11][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[C:9]([CH3:20])[CH:8]=2)=[O:33]

참가 물질

6

반응물 3

HCID 222AmmoniaHCID 5152919Cesium acetateHCID 58437218(Z)-3-(5-benzyloxy-2-bromo-4-methylphenyl)-2-benzyloxycarbonylaminoacrylic acid methyl ester

생성물 1

HCID 584374865-Benzyloxy-6-methyl-1H-indole-2-carboxylic acid methyl ester수율 63.1%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
90 °C

실험 절차

To a solution of (Z)-3-(5-benzyloxy-2-bromo-4-methylphenyl)-2-benzyloxycarbonylaminoacrylic acid methyl ester (0.2 g) and copper (I) iodide (0.075 g) in dimethylsulfoxide (8 mL) was added cesium acetate (0.38 g) at room temperature and this mixture was stirred under argon atmosphere at 90° C. for 5 hours. To this reaction mixture was added aqueous ammonia solution (28%) and the precipitated solid was collected by filtration, and washed with water, dried under reduced pressure to give the title compound (0.073 g).

후처리

  1. filtrationthe precipitated solid was collected by filtration
  2. washwashed with water
  3. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-865e985d28cb44e48a972d7c9f48d8fb
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829040B2

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