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

HRID 16627노트

반응식

HRID 16627 반응식
[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]

참가 물질

8

반응물 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 1452113,5-DifluorobenzylamineHCID 497872521-benzyl-5-hydroxy-2-methyl-1H-indole-3-carboxylic acid2회

생성물 1

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

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-7a9e2327eeae4ef0891cfeb4d4e60298
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737173B2

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