5-Bromo-2-methoxy-3-methylpyridine → 6-Methoxy-5-methylnicotinonitrile

HRID 1753218ノート

反応式

HRID 1753218 の反応式
Br[C:2]1[CH:3]=[C:4]([CH3:10])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[C:11]([Cu])#[N:12]>CN(C=O)C.CCOC(C)=O>[C:11]([C:2]1[CH:3]=[C:4]([CH3:10])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1)#[N:12]

参加物

5

反応物 2

HCID 225911765-Bromo-2-methoxy-3-methylpyridineHCID 178418546HCID 178418546、化合物

生成物 1

HCID 534159886-Methoxy-5-methylnicotinonitrile収率 93%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 5-bromo-2-methoxy-3-methyl-pyridine (1.0 g, 5.0 mmol) in DMF (10 ml) was added CuCN (0.534 g, 6.0 mmol) and the resulting mixture is heated at reflux for 28 h. After cooling to room temperature the mixture is diluted with EtOAc and washed with 10% ammonia solution followed by water and brine solution. The organic layer was separated, dried over MgSO4 and evaporated under reduced pressure. The residue was purified by flash chromatography (5% EtOAc/Hexane) to give 5-cyano-2-methoxy-3-methyl-pyridine (36) (0.68 g, 93%).

後処理

  1. temperaturethe resulting mixture is heated
  2. temperatureat reflux for 28 h
  3. washwashed with 10% ammonia solution
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography (5% EtOAc/Hexane)

出典と根拠

ORDレコード
ord-3331207347604db1bc03788b882b2c3f
出典データセット
uspto-grants-2015_10
特許番号
US09163020B2

反応ノート

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