Diisopropylamine → HCID 178488436, compound

Participants

Reaction Conditions

Reaction Steps

A solution of LDA (2.4 mmol) was prepared by adding n-BuLi (1.7 mL, 2.4 mmol, 1.4 M in hexanes) via syringe to a solution of diisopropylamine (247 mg, 2.4 mmol) in THF (10 mL) at 0° C. and stirring for 15 minutes. The solution was then cooled to −40° C., then 2-methyl-6-trifluoromethylnicotinic acid (250 mg, 1.2 mmol) in THF (5 mL) was added via syringe. After stirring at −40° C. for 30 minutes, 4-methoxybenzonitrile (162 mg, 1.2 mmol) in THF (5 mL) was added via syringe. The reaction mixture was allowed to warm to room temperature and stirred for 16 hours. The reaction was quenched by addition of sat. NH4Cl solution. A precipitate formed which was collected by vacuum filtration giving the title compound (150 mg, 40%) as an off white solid.

Provenance & Evidence