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

HRID 1511074Notes

Reaction equation

HRID 1511074 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ed0225753da04d579d82ae8be5b0c3c4
Source dataset
uspto-grants-2012_07
Patent number
US08212045B2

Reaction notes

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