Nitrogen → HCID 54471613, compound

Participants

Reaction Conditions

Reaction Steps

In a screw top flask 3-aminoethylphenylboronic acid hydrochloride (10.0 g, 53.4 mmol), 4-bromobenzotrifluoride (12.0, 53.4 mmol) and potassium phosphate (34.0 g, 160.2 mmol) were combined in dimethoxyethane (50 mL) and water (10 mL). The flask was flushed with N2 and tetrakis(triphenylphosphine)palladium (3.10 g, 2.67 mmol) was added. The flask was sealed and heated to 120° C. for 12 hours. The reaction mixture was cooled to rt and H2O (100 mL) was added and the resulting mixture was extracted with EtOAc (3×25 mL). The organic phases were combined, washed with brine (20 mL), dried with Na2SO4, filtered, concentrated and purified by flash column chromatography (0%-20% of a 10% NH3 in CH2Cl2 in CH2Cl2) providing the desired product as a brown oil (8.7 g, 69%). MS (ESI): mass calcd. for C14H12F3N, 251.25; m/z found 252.1 [M+H]+. 1H NMR (500 MHz, DMSO) δ 7.90 (d, J=8.1, 2H), 7.82 (d, J=8.2, 2H), 7.71 (s, 1H), 7.56 (d, J=7.5, 1H), 7.44 (t, J=7.5, 1H), 7.39 (d, J=7.5, 1H), 3.79 (s, 2H), 1.86 (s, 2H).

Provenance & Evidence