1-Propanol → 3-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-ethenylbenzonitrile

Participants

Reaction Conditions

Reaction Steps

3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-bromobenzonitrile (0.70 g, 1.969 mmol) was combined with potassium vinyl trifluoroborate (0.396 g, 2.95 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), dichloromethane complex (1:1) (0.058 g, 0.079 mmol) and TEA (0.412 mL, 2.95 mmol) in n-propanol (10 mL) and heated in a microwave reactor at 120° C. for 30 min. The reaction mixture was filtered through Celite™ and concentrated to dryness. The residue was dissolved in DCM, washed with saturated aqueous NaHCO3, dried over MgSO4, filtered and concentrated to dryness. The crude material was purified on silica gel (eluted with 0 to 10% CH3OH/DCM) to give 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-ethenylbenzonitrile (0.52 g, 1.718 mmol, 87% yield) as an orange solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.79 (s, 1H), 7.45-7.55 (m, 2H), 7.40 (s, 1H), 7.25 (s, 1H), 6.75 (dd, 1H), 6.04 (d, 1H), 5.43 (d, 1H), 3.77 (s, 2H), 2.05 (br. s., 2H). LC-MS (ES+) m/z 303.32, 305.30 [M+H].

Provenance & Evidence