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

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Reaction Conditions

Reaction Steps

A mixture of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-bromobenzonitrile (0.62 g, 1.744 mmol), tributyl(2-propen-1-yl)stannane (0.924 g, 2.79 mmol) and Pd(PPh3)4 (0.201 g, 0.174 mmol) in N,N-Dimethylformamide (DMF) (14 ml) was heated in a microwave reactor at 120° C. for 30 min. The vessel was cooled to RT and ethyl acetate (200 mL) and water (200 mL) were added. The organic layer was separated, washed with brine (200 mL), dried over MgSO4, filtered and concentrated. The crude material was purified on silica gel (hexanes/ethyl acetate) to give 0.38 g of a mixture of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(2-propen-1-yl)benzonitrile and Bu3SnBr. The material was used without further purification. N4011-30-100. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.20-7.29 (m, 2H), 7.17 (s, 1H), 7.02 (s, 1H), 6.84 (s, 1H), 5.78-5.96 (m, 1H), 5.01-5.18 (m, 2H), 3.91 (s, 2H), 3.37 (d, 2H).

Provenance & Evidence