Water → 5-Bromo-3-(2,6-dimethylpyridin-3-yloxy)picolinonitrile

HRID 1511023

반응식

HRID 1511023 반응식
[CH3:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.[H-].[Na+].[Br:12][C:13]1[CH:14]=[C:15]([N+]([O-])=O)[C:16]([C:19]#[N:20])=[N:17][CH:18]=1.O>CN(C=O)C>[Br:12][C:13]1[CH:14]=[C:15]([O:8][C:7]2[C:2]([CH3:1])=[N:3][C:4]([CH3:9])=[CH:5][CH:6]=2)[C:16]([C:19]#[N:20])=[N:17][CH:18]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 707322,6-Dimethyl-3-pyridinolHCID 27696985-Bromo-3-nitropyridine-2-carbonitrile

생성물 1

HCID 674864525-Bromo-3-(2,6-dimethylpyridin-3-yloxy)picolinonitrile수율 101.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a 0° C. solution of 2,6-dimethylpyridin-3-ol (10 g, 81.2 mmol) in DMF (50 ml) was added sodium hydride (60% dispersion in oil, 3.4 g, 85 mmol). After 15 minutes, 5-bromo-3-nitropicolinonitrile (18.5 g, 81 mmol) was added and the mixture was allowed to warm slowly to ambient temperature. The reaction mixture was slowly added to 500 mL of rapidly stirring water. A light red solid formed and then the material formed a gum. The gum was extracted into ethyl acetate, and the organics washed with brine, dried over MgSO4 and concentrated in vacuo to afford 5-bromo-3-(2,6-dimethylpyridin-3-yloxy)picolinonitrile (25 g, 82 mmol, 101% yield).

후처리

  1. customA light red solid formed
  2. customthe material formed a gum
  3. extractionThe gum was extracted into ethyl acetate
  4. washthe organics washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-df9d5f886d404ab9804c313940d032ff
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08212045B2

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