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4-[2-Carbamoyl-1-(3-fluoro-benzyl)-1H-indol-4-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester → 4-[2-carbamoyl-1-(3-fluoro-benzyl)-1H-indol-4-yl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 18163
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인쇄 미리보기

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HRID 18163 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[C:17]([C:31](=[O:33])[NH2:32])[N:18]3[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[C:17]([C:31](=[O:33])[NH2:32])[N:18]3[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

4

반응물 1

HCID 685845934-[2-Carbamoyl-1-(3-fluoro-benzyl)-1H-indol-4-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 685859844-[2-carbamoyl-1-(3-fluoro-benzyl)-1H-indol-4-yl]-piperidine-1-carboxylic acid tert-butyl ester수율 48.1%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

4-[2-Carbamoyl-1-(3-fluoro-benzyl)-1H-indol-4-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (156 mg, 0.35 mmol) in EtOH (20 ml) was added to a Parr vessel containing catalytic amount of 5% Pd on carbon. The vessel was purged with H2 at the pressure of 50 psi (3.45 bar). After shaking overnight, the reaction mixture was filtered through Celite and concentrated. The brown residue was purified by flash chromatography to give 4-[2-carbamoyl-1-(3-fluoro-benzyl)-1H-indol-4-yl]-piperidine-1-carboxylic acid tert-butyl ester as yellow solid (76 mg, 48%).

후처리

  1. customThe vessel was purged with H2 at the pressure of 50 psi (3.45 bar)
  2. filtrationthe reaction mixture was filtered through Celite
  3. concentrationconcentrated
  4. customThe brown residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-fe8e3ab991134d0ebb273f0706bbddff
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07741326B2

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