Acetic Acid → N-(1H-Pyrrolo[2,3-c]pyridin-5-yl)acetamide

HRID 875383노트

반응식

HRID 875383 반응식
CN(C)/[CH:3]=[CH:4]\[C:5]1[C:10]([N+:11]([O-])=O)=[CH:9][N:8]=[C:7]([NH:14][C:15](=[O:17])[CH3:16])[CH:6]=1.C(O)(=O)C>CO.ClCCl.[Pd]>[NH:11]1[C:10]2=[CH:9][N:8]=[C:7]([NH:14][C:15](=[O:17])[CH3:16])[CH:6]=[C:5]2[CH:4]=[CH:3]1

참가 물질

6

반응물 2

HCID 176Acetic AcidHCID 86720622N-{4-[(Z)-2-(dimethylamino)ethenyl]-5-nitropyridin-2-yl}acetamide

생성물 1

HCID 18975304N-(1H-Pyrrolo[2,3-c]pyridin-5-yl)acetamide수율 71%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

To a solution of N-{4-[(Z)-2-(dimethylamino)ethenyl]-5-nitropyridin-2-yl}acetamide (0.7 g, 3 mmol, Step b) in methanol and dichloromethane (5:1, 120 mL), palladium on carbon (0.4 g) was added followed by addition of acetic acid (7 mL). The reaction mixture was then purged with hydrogen gas and stirred overnight at room temperature. The resulting mixture was filtered over celite bed, and the residue was washed with methanol (100 mL). The combined filtrate was concentrated under vacuum and purified by silica gel column chromatography using methanol in dichloromethane (2%) to afford N-(1H-pyrrolo[2,3-c]pyridin-5-yl)acetamide (0.35 g, 71%).

후처리

  1. customThe reaction mixture was then purged with hydrogen gas
  2. filtrationThe resulting mixture was filtered over celite bed
  3. washthe residue was washed with methanol (100 mL)
  4. concentrationThe combined filtrate was concentrated under vacuum
  5. custompurified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-51e9f70625834fada9fe65e36c7b0bfb
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08980911B2

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