2-Bromopyridine → HCID 10494836, compound

Participants

Reaction Steps

A solution of 2-bromopyridine (0.47 g) in anhydrous tetrahydrofuran (5 ml) was cooled to -78° C. and 1.6M n-butyllithium in hexane (2.1 ml) was added dropwise under an argon atmosphere. The mixture was stirred for 30 minutes. Then, a solution of 2-cyano-4-trifluoromethylphenol (0.19 g) in anhydrous tetrahydrofuran (5 ml) was added to the reaction mixture and the resulting mixture was stirred at -78° C. for an additional 1 hour. The reaction was quenched by adding acetic acid (0.18 g) to the reaction mixture and the solvent was distilled off under reduced pressure. Ammonium acetate (2 g) and 2,2-dimethoxypropane (5 ml) were added to the residue and the mixture was heated under reflux for 3 hours. The solvent was distilled off and the residue was extracted by addition of ethyl acetate and aqueous sodium bicarbonate solution. The ethyl acetate layer was washed with saturated saline solution and dried over anhydrous magnesium sulfate and the solvent was distilled off. The residue was purified by column chromatography on silica gel to obtain 6-trifluoromethyl-2,2-dimethyl-4-(2-pyridyl)-2H-1,3-benzoxazine (0.19 g) (Compound 74).

Provenance & Evidence