Potassium Carbonate → (E)-2-amino-6-(3-methoxyprop-1-enyl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-amino-6-bromobenzonitrile (1.0 g, 5.0 mmol), (E)-2-(3-methoxypropenyl)-4,4,5,5-tetramethyl-(1,3,2)-dioxaboroane (1.2 g, 6.0 mmol), and K2CO3 (1.38 g, 10.0 mmol) in DME/H2O (4:1, 20 mL) was added Pd(PPh3)4 (289 mg) at room temperature under nitrogen. The reaction mixture was warmed to 85° C. and stirred at that temperature under nitrogen overnight. After it was cooled down to room temperature, the reaction solution was diluted with EtOAc, washed with brine (2×), and dried over Na2SO4. After removal of the solvent, the residue was purified by chromatography on silica gel eluting with 30% EtOAc in hexanes to give the title compound as a pale-yellow solid. 1H NMR (400 MHz, CDCl3) δ 3.40 (s, 3H), 4.12 (dd, J=6.0, 1.8 Hz, 2H), 4.42 (s, 2H), 6.42 (dt, J=16.0, 5.8 Hz, 1H), 6.63 (d, J=8.0 Hz, 1H), 6.85 (d, J=16.0 Hz, 1H), 6.93 (d, J=8.0 Hz, 1H), 7.26 (t, J=8.0 Hz, 1H). 13C NMR (CDCl3) δ 58.2, 72.7, 95.4, 113.6, 115.0, 116.6, 128.5, 130.9, 133.4, 140.3, 150.1. MS 189 (MH+).

Provenance & Evidence