1,2-Dichloroethane → 1-benzyl-5-hydroxy-2-methyl-1H-indole-3-carboxylic acid, 3,5-difluorobenzylamide

HRID 16627

反応式

HRID 16627 の反応式
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[C:10]([C:18]([OH:20])=O)=[C:9]1[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[F:36][C:37]1[CH:38]=[C:39]([CH:42]=[C:43]([F:45])[CH:44]=1)[CH2:40][NH2:41]>C(Cl)Cl.CN(C=O)C.CCOC(C)=O>[F:36][C:37]1[CH:38]=[C:39]([CH:42]=[C:43]([F:45])[CH:44]=1)[CH2:40][NH:41][C:18]([C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=2)[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]=1[CH3:21])=[O:20]

参加物

8

反応物 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 1452113,5-DifluorobenzylamineHCID 497872521-benzyl-5-hydroxy-2-methyl-1H-indole-3-carboxylic acid2 回

生成物 1

HCID 248041181-benzyl-5-hydroxy-2-methyl-1H-indole-3-carboxylic acid, 3,5-difluorobenzylamide

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 1-benzyl-5-hydroxy-2-methyl-1H-indole-3-carboxylic acid (Compound 2, 205 mg, 0.73 mmol) in CH2Cl2 (5 ml) and DMF (3 ml) was added EDC (211 mg, 1.1 mmol), HOBT (149 mg, 1.1 mmol) and 3,5-difluorobenzylamine (260 μl, 2.2 mmol). The mixture was stirred at room temperature for 16 h, diluted with EtOAc, and washed with 1M HCl, and brine, and dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (30% to 50% EtOAc-hexanes) to yield 1-benzyl-5-hydroxy-2-methyl-1H-indole-3-carboxylic acid, 3,5-difluorobenzylamide (Compound 3) as a beige solid.

後処理

  1. washwashed with 1M HCl, and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash column chromatography on silica gel (30% to 50% EtOAc-hexanes)

出典と根拠

ORDレコード
ord-7a9e2327eeae4ef0891cfeb4d4e60298
出典データセット
uspto-grants-2010_06
特許番号
US07737173B2

関連ノート

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