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

HRID 16634ノート

反応式

HRID 16634 の反応式
[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]

参加物

3

反応物 1

HCID 589447245-benzyloxy-2-methyl-1-phenyl-1H-indole-3-carboxylic acid, 3,4-difluoro-benzylamide2 回

生成物 1

HCID 24804767HCID 24804767、化合物収率 92%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-b67d2a2af3e84a65b22ba81bd6e15ab7
出典データセット
uspto-grants-2010_06
特許番号
US07737173B2

反応ノート

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