Imidazole → 5-(1H-imidazol-1-yl)picolinonitrile

HRID 2281875ノート

反応式

HRID 2281875 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[NH:10]1[CH:14]=[CH:13][N:12]=[CH:11]1>CN(C)C=O>[N:10]1([C:2]2[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=2)[CH:14]=[CH:13][N:12]=[CH:11]1

参加物

4

反応物 2

HCID 795ImidazoleHCID 8171545-Bromopyridine-2-carbonitrile

生成物 1

HCID 671513405-(1H-imidazol-1-yl)picolinonitrile収率 66.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

5-bromopicolinonitrile (2.0 g, 10.9 mmol), imidazole (818 mg, 12 mmol) potassium carbonate (1.66 g, 12 mmol) and dimethylformamide (40 mL) were combined and heated to 130° C. for 20 hours. The reaction solution was evaporated and the residue was partitioned between dichloromethane (150 mL) and water (100 mL). The phases were separated and the organic phase was washed with water (50 mL), dried over magnesium sulfate and evaporated to give a residue which was purified by flash chromatography eluting with 2-3% methanol in dichloromethane gradient to give 5-(1H-imidazol-1-yl)picolinonitrile (1.23 g, 66%).

後処理

  1. customThe reaction solution was evaporated
  2. customthe residue was partitioned between dichloromethane (150 mL) and water (100 mL)
  3. customThe phases were separated
  4. washthe organic phase was washed with water (50 mL)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customto give a residue which
  8. customwas purified by flash chromatography
  9. washeluting with 2-3% methanol in dichloromethane gradient

出典と根拠

ORDレコード
ord-74358134aa594bbf8030c8a557229af9
出典データセット
uspto-grants-2015_09
特許番号
US09139587B2

反応ノート

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