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

HRID 534056ノート

反応式

HRID 534056 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6a5adb6877ee4547bb07c0e4688aef60
出典データセット
uspto-grants-2014_10
特許番号
US08853409B2

反応ノート

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