Tetrahydrofuran → 2-(3,5-Bis-trifluoromethyl-phenyl)-N-(6'-chloro-2-methyl-[3,4]bipyridinyl-3'-yl)-N-methyl-isobutyramide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2.77 g (11.9 mmol) (6′-chloro-2-methyl-[3,4′]bipyridinyl-3′-yl)-methyl-amine in 120 ml tetrahydrofuran 7.8 ml (12 mmol) of a 1.6 M solution of n-butyllithium in hexanes was added dropwise at −78° C. After 30 min. 4.2 g (13 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride were added. The reaction mixture was stirred at −78° C. for 5 min. and allowed to warm to room temperature during a period of 1 h. Dilution with 2 M aqueous sodium carbonate solution was followed by extraction with three portions of tert-butyl methyl ether. The combined organic layers were washed with 2 M aqueous sodium carbonate solution and brine, dried over sodium sulfate and concentrated in vacuo. Flash column chromatography gave 4.8 g (78%) of the title compound as an off-white solid.

Provenance & Evidence