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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence