Sodium hydride → 5-Bromo-3-(2,4-dimethylpyridin-3-yloxy)picolinonitrile

HRID 534056노트

반응식

HRID 534056 반응식
[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([CH3:9])[CH:5]=[CH:4][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.[NH4+].[Cl-]>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][CH:4]=[CH:5][C:6]=2[CH3:9])[C:16]([C:19]#[N:20])=[N:17][CH:18]=1

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27696985-Bromo-3-nitropyridine-2-carbonitrileHCID 150473662,4-Dimethyl-3-hydroxypyridine

생성물 1

HCID 674859525-Bromo-3-(2,4-dimethylpyridin-3-yloxy)picolinonitrile수율 92.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A flask was charged with 2,4-dimethylpyridin-3-ol (9.0 g, 73.1 mmol) and DMF (80 mL) was added. Sodium hydride (2.03 g, 80.4 mmol) was added and the reaction was stirred for 15 minutes. 5-Bromo-3-nitropicolinonitrile (16.7 g, 73.1 mmol) was added and the reaction was stirred for 25 minutes. The reaction mixture was poured into 600 mL saturated NH4Cl and 600 mL water and then filtered, washed with water and a small amount of hexanes, and dried over high vacuum to provide 5-bromo-3-(2,4-dimethylpyridin-3-yloxy)picolinonitrile (20.5 g, 67.4 mmol, 92.2% yield) as a light tan solid.

후처리

  1. additionwas added
  2. stirringthe reaction was stirred for 25 minutes
  3. filtrationfiltered
  4. washwashed with water
  5. dry with materiala small amount of hexanes, and dried over high vacuum

출처 및 근거

ORD 기록
ord-6a5adb6877ee4547bb07c0e4688aef60
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853409B2

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