Dimethylformamide → 2-(4-bromo-pyridin-2-yl)-2-cyano-N,N-dimethyl-acetamide

HRID 886573노트

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HRID 886573 반응식
[H-].[Na+].[C:3]([CH2:5][C:6]([N:8]([CH3:10])[CH3:9])=[O:7])#[N:4].[Br:11][C:12]1[CH:17]=[C:16]([Br:18])[CH:15]=[CH:14][N:13]=1.[CH3:19][N:20]([CH3:23])C=O>>[Br:18][C:16]1[CH:15]=[CH:14][N:13]=[C:12]([CH:5]([C:3]#[N:4])[C:6]([N:8]([CH3:10])[CH3:9])=[O:7])[CH:17]=1.[Br:11][C:12]1[CH:19]=[N:20][CH:23]=[CH:16][C:17]=1[CH:5]([C:3]#[N:4])[C:6]([N:8]([CH3:10])[CH3:9])=[O:7]

참가 물질

6

반응물 4

HCID 6228Dimethylformamide2회HCID 24758Sodium hydrideHCID 2511432-Cyano-N,N-dimethylacetamideHCID 8171042,4-Dibromopyridine

생성물 2

HCID 598250762-(4-bromo-pyridin-2-yl)-2-cyano-N,N-dimethyl-acetamideHCID 689600462-(3-bromo-pyridin-4-yl)-2-cyano-N,N-dimethyl-acetamide

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온도
60 °C

실험 절차

Sodium hydride (186.2 mg, 4.65 mmol, 60% dispersion in oil) was added to a solution of 2-cyano-N,N-dimethyl-acetamide (373.7 mg, 3.33 mmol) in dimethylformamide (10 mL) at 0° C. The mixture was removed from the ice bath for 20 min, and a solution of 2,4-dibromopyridine (300 mg, 1.33 mmol) in dimethylformamide (3 mL) was quickly added. The mixture was heated at 60° C. for 16 h. The reaction was cooled to room temperature, quenched by addition of 200 μL saturated ammonium chloride and concentrated to a residue. The compound was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes to afford 2-(4-bromo-pyridin-2-yl)-2-cyano-N,N-dimethyl-acetamide and 2-(3-bromo-pyridin-4-yl)-2-cyano-N,N-dimethyl-acetamide.

후처리

  1. customThe mixture was removed from the ice bath for 20 min
  2. temperatureThe reaction was cooled to room temperature
  3. customquenched by addition of 200 μL saturated ammonium chloride
  4. concentrationconcentrated to a residue
  5. customThe compound was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-dbd686e09898417da4dfc09ec43f2c80
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242280B2

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