Dibah → 1-Benzyl-N-(3,4-difluorobenzyl)-6-(hydroxymethyl)-2-isopropyl-1H-indole-3-carboxamide

HRID 40076

반응식

HRID 40076 반응식
C([O:3][C:4]([C:6]1[CH:14]=[C:13]2[C:9]([C:10]([C:25](=[O:36])[NH:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([F:34])=[C:30]([F:35])[CH:29]=3)=[C:11]([CH:22]([CH3:24])[CH3:23])[N:12]2[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:8][CH:7]=1)=O)C.CC(C[Al]CC(C)C)C>C(Cl)Cl>[CH2:15]([N:12]1[C:13]2[C:9](=[CH:8][CH:7]=[C:6]([CH2:4][OH:3])[CH:14]=2)[C:10]([C:25]([NH:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[C:30]([F:35])[CH:29]=2)=[O:36])=[C:11]1[CH:22]([CH3:24])[CH3:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

4

반응물 2

HCID 16682954DibahHCID 25060002Ethyl1-Benzyl-3-(3,4-difluorobenzylcarbamoyl)-2-isopropyl-1H-indole-6-carboxylate2회

생성물 1

HCID 250602611-Benzyl-N-(3,4-difluorobenzyl)-6-(hydroxymethyl)-2-isopropyl-1H-indole-3-carboxamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of ethyl1-benzyl-3-(3,4-difluorobenzylcarbamoyl)-2-isopropyl-1H-indole-6-carboxylate (Compound 43, 200 mg, 0.408 mmol) in CH2Cl2 (10 ml) at −78° C. under argon was added Dibal-H (1.0 M in CH2Cl2, 1.6 ml, 1.63 mmol) slowly. The reaction was stirred for 3 h, quenched with methanol, celite, diluted with EtOAc, washed with H2O, brine, dried over Na2SO4, concentrated in vacuo. The residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes) to yield the title compound as a white solid.

후처리

  1. customquenched with methanol, celite
  2. additiondiluted with EtOAc
  3. washwashed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes)

출처 및 근거

ORD 기록
ord-23847c78625d42f6b68eb021c0c46262
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524917B2

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