5-benzyloxy-2-methyl-1-phenyl-1H-indole-3-carboxylic acid, 3,4-difluoro-benzylamide → HCID 24804767, 화합물

HRID 16634노트

반응식

HRID 16634 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][C:35]=1[F:36])[CH2:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18]CC3C=CC=CC=3)[CH:16]=2)[N:11]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:10]=1[CH3:32])=[O:8]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][C:35]=1[F:36])[CH2:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=2)[N:11]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:10]=1[CH3:32])=[O:8]

참가 물질

3

반응물 1

HCID 589447245-benzyloxy-2-methyl-1-phenyl-1H-indole-3-carboxylic acid, 3,4-difluoro-benzylamide2회

생성물 1

HCID 24804767HCID 24804767, 화합물수율 92%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a mixture of 5-benzyloxy-2-methyl-1-phenyl-1H-indole-3-carboxylic acid, 3,4-difluoro-benzylamide (Compound 56, 0.15 g, 0.31 mmol) in methanol (15 ml), which was degassed with argon for 10 min, was added 10% palladium on carbon (0.17 g), with continued degassing. The reaction was placed in par tube on hydrogenator and hydrogenated at 45 psi for 18 h. The reaction was then filtered, concentrated under reduced pressure and the crude product residue was purified by flash column chromatography on silica gel (30% EtOAc-hexanes) to yield 5-hydroxy-2-methyl-1-phenyl-1H-indole-3-carboxylic acid, 3,4-difluorobenzylamide (Compound 29) as a solid (0.11 g, 92%).

후처리

  1. customwas degassed with argon for 10 min
  2. additionwas added 10% palladium on carbon (0.17 g)
  3. filtrationThe reaction was then filtered
  4. concentrationconcentrated under reduced pressure
  5. customthe crude product residue was purified by flash column chromatography on silica gel (30% EtOAc-hexanes)

출처 및 근거

ORD 기록
ord-b67d2a2af3e84a65b22ba81bd6e15ab7
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737173B2

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