Allyltributylstannane → 3-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(2-propen-1-yl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-bromobenzonitrile (0.300 g, 0.844 mmol), allyltributyl tin (0.414 mL, 1.350 mmol) and tetrakis(triphenylphosphine) palladium(0) (0.097 g, 0.084 mmol) were combined in DMF (7 mL), purged with nitrogen, and heated at 160° C. in a microwave reactor for 30 min. The reaction mixture was filtered through Celite, diluted with EtOAc, and washed four times with dilute aqueous NaHCO3. The organic phase was isolated, dried over MgSO4, filtered and concentrated to dryness. The residue was purified on 40 g silica gel eluted successively with EtOAc followed by 0 to 10% CH3OH/DCM to give 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(2-propen-1-yl)benzonitrile (0.145 g, 0.458 mmol, 54.3% yield) as a clear oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.45-7.53 (m, 2H), 7.42 (s, 1H), 7.22 (s, 1H), 7.13 (s, 1H), 5.87-6.00 (m, 1H), 5.04-5.14 (m, 2H), 3.76 (s, 2H), 3.41 (d, J=6.59 Hz, 2H), 2.18-2.46 (br. s., 2H). LC-MS (ES−) m/z 315.20, 317.08 [M−1]. LC-MS (ES+) m/z 317.31, 319.31 [M+H].

Provenance & Evidence