Ethyl orthoformate → HCID 59375009, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-amino-5-fluorobenzoic acid (1.00 g, 6.45 mmol), 3-bromo-2-methylaniline (1.199 g, 6.45 mmol) and triethoxymethane (0.955 g, 6.45 mmol) in THF (2 mL) was heated at 110° C. overnight in a sealed tube. The mixture was cooled to rt and diluted with EtOAc. The solution was washed with NaHCO3 (aq) and water, then was dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from 80:20 to 70:30 hexane-EtOAc) to give 3-(3-bromo-2-methylphenyl)-6-fluoroquinazolin-4(3H)-one as a white solid (1.2 g, 56%). 1H NMR (400 MHz, chloroform-d) δ 8.00 (1 H, dd, J=8.4, 3.1 Hz), 7.93 (1 H, s), 7.81 (1 H, dd, J=9.0, 4.8 Hz), 7.74 (1 H, dd, J=6.9, 2.3 Hz), 7.50-7.58 (1 H, m), 7.21-7.26 (2 H, m), 2.25 (3 H, s). Mass spectrum m/z 333, 335 (M+H)+.

Provenance & Evidence