(+-)-2-Butanol → Tert-butyl 2-(2',3-difluoro-2,4'-bipyridin-5-yl)acetate

Participants

Reaction Conditions

Reaction Steps

To a flask containing tert-butyl 2-(6-chloro-5-fluoropyridin-3-yl)acetate 205-3 (370 mg, 1.5 mmol), 2-fluoropyridin-4-ylboronic acid 205-4 (318 mg, 2.25 mmol), Pd(OAc)2 (17 mg, 0.075 mmol.), 2-dicyclohexylphosphino-2′,6′-dimethoxyybiphenyl (62 mg, 0.15 mmol), K3PO4 (800 mg, 9 mmol) under argon was added 2-butanol (1.5 mL). The reaction mixture was stirred at 100° C. for 10 hours. After cooled to room temperature, the mixture was diluted with ethyl acetate, washed with water and brine, dried over Na2SO4, and concentrated to dryness by rotary evaporation. The crude was purified by silica gel flash chromatography, eluted with 20% ethyl acetate in dichloromethane to give tert-butyl 2-(2′,3-difluoro-2,4′-bipyridin-5-yl)acetate 205-5 as a yellow oil. MS m/z 307.1 (M+1).

Provenance & Evidence