Dimethylformamide → HCID 59593351, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (5-bromo-pyridin-2-yl)-(4-trifluoromethyl-benzyl)-amine (21, 3.55 g, 0.0107 mol) in tetrahydrofuran (150 mL), tert-butyllithium (13.2 mL, 1.70 M in pentane, 0.0224 mol) was added slowly under an atmosphere of nitrogen at −78° C. over 10 minutes. The reaction mixture was stirred at −78° C. for 90 minutes. N,N-Dimethylformamide (2.2 mL, 0.028 mol) was added slowly into the reaction mixture. The reaction mixture was stirred at −78° C. for 2 hours, then allowed to warm to room temperature. After stirring at room temperature for 2 hours, the reaction mixture was poured into ice water and extracted with ethyl acetate. The organic phase was washed with saturated sodium bicarbonate, brine, and dried over magnesium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with ethyl acetate in hexane to provide the compound as a light yellow solid (22, 1.67 g, 56%).

Provenance & Evidence