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

HRID 1753218노트

반응식

HRID 1753218 반응식
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]

참가 물질

5

반응물 2

HCID 225911765-Bromo-2-methoxy-3-methylpyridineHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 534159886-Methoxy-5-methylnicotinonitrile수율 93%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-3331207347604db1bc03788b882b2c3f
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09163020B2

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