Sodium hydride → 5-bromo-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinonitrile

HRID 534090

Reaction equation

HRID 534090 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([OH:8])[C:4]([CH3:9])=[N:3]1.CN(C=O)C.O1CCOCC1.[H-].[Na+].[Br:23][C:24]1[CH:25]=[C:26]([N+]([O-])=O)[C:27]([C:30]#[N:31])=[N:28][CH:29]=1>O>[Br:23][C:24]1[CH:25]=[C:26]([O:8][C:5]2[C:4]([CH3:9])=[N:3][N:2]([CH3:1])[C:6]=2[CH3:7])[C:27]([C:30]#[N:31])=[N:28][CH:29]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 27696985-Bromo-3-nitropyridine-2-carbonitrileHCID 12498505trimethyl-1H-pyrazol-4-olHCID 217120691,4-dioxane N,N-dimethylformamide

Product 1

HCID 674868715-bromo-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinonitrileYield 97.74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A flask was charged with 1,3,5-trimethyl-1H-pyrazol-4-ol (10.46 g, 82.89 mmol), and DMF:dioxane (9:1) (700 mL). The reaction mixture was cooled to 0° C. and 60% sodium hydride (3.315 g, 82.89 mmol) was added portionwise. The reaction mixture was stirred for 15 minutes, and 5-bromo-3-nitropicolinonitrile (18 g, 78.95 mmol) was added. The reaction was stirred at ambient temperature for 3 hours, then poured slowly into 600 mL water and stirred for 10 minutes. The resultant solids were filtered and dried to afford 5-bromo-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinonitrile (23.70 g, 97.74% yield) as very lightly tan (white) solid.

Workup

  1. stirringThe reaction was stirred at ambient temperature for 3 hours
  2. stirringstirred for 10 minutes
  3. filtrationThe resultant solids were filtered
  4. customdried

Sources & evidence

ORD record
ord-817ab481f4c5422187b675760b23802f
Source dataset
uspto-grants-2014_10
Patent number
US08853409B2

Linked notes

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