Sodium Cyanide → 5-Bromo-4-methylpyridine-2-carbonitrile

HRID 717139

반응식

HRID 717139 반응식
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Br:9])=[CH:4][N:3]=1.[Cu](C#N)[C:11]#[N:12].[C-]#N.[Na+]>CN(C)C=O>[Br:9][C:5]1[C:6]([CH3:8])=[CH:7][C:2]([C:11]#[N:12])=[N:3][CH:4]=1

참가 물질

5

반응물 3

HCID 8929Sodium CyanideHCID 27344292,5-Dibromo-4-methylpyridineHCID 178418260HCID 178418260, 화합물

생성물 1

HCID 533954685-Bromo-4-methylpyridine-2-carbonitrile수율 73%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
158 °C

실험 절차

2,5-Dibromo-4-methylpyridine (5.0 g, 19.9 mmol), copper cyanide (1.43 g, 15.9 mmol), sodium cyanide (0.801 g, 16.3 mmol) and dimethylformamide (30 mL) were combined in a sealed reaction vessel and heated at 158° C. for 3 h. The reaction mixture was purified by silica gel column chromatography (0-80% ethyl acetate in hexanes). The resulting material was subjected to a second silica gel column (0-20% methanol in dichloromethane). Clean fractions were combined and concentrated to afford the title compound as a white solid (2.30 g, 11.6 mmol, 58% yield). MS (ESI) m/z 198.0 [M+1]+.

후처리

  1. customThe reaction mixture was purified by silica gel column chromatography (0-80% ethyl acetate in hexanes)
  2. concentrationconcentrated

출처 및 근거

ORD 기록
ord-da3a44de34f24762aad41bf794de1e20
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193692B2

연결된 노트

불러오는 중…