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

HRID 886573ノート

反応式

HRID 886573 の反応式
[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]

参加物

6

反応物 4

HCID 6228Dimethylformamide2 回HCID 24758Sodium hydrideHCID 2511432-Cyano-N,N-dimethylacetamideHCID 8171042,4-Dibromopyridine

生成物 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

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-dbd686e09898417da4dfc09ec43f2c80
出典データセット
uspto-grants-2012_08
特許番号
US08242280B2

反応ノート

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