Methanol → HCID 82547484, compound

Participants

Reaction Steps

A mixture of 2-amino-3-bromo-benzoic acid (2 g, 9.26 mmol), HATU (3.84 g, 10.10 mmol, Sigma Aldrich), DMF (42.1 mL), 2.0 M ethylamine in MeOH (4.21 mL, 8.42 mmol, Sigma Aldrich), and TEA (1.8 mL, 12.62 mmol) was set stirring at RT for 18 h. It was diluted with water and extracted with EtOAc. The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure. It was diluted with DCM, adsorbed onto silica, and purified on 40 g SiO2 (eluent: 0-100% EtOAc/hexanes over 25 min, RediSep Gold). The product fractions were combined and concentrated to give the product as a yellow oil (2.5 g, 122%). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.39 (1H, br. s.) 7.47-7.54 (2H, m) 6.52 (1H, t, J=7.82 Hz) 6.44 (2H, br. s.) 3.19-3.29 (2H, m) 1.11 (3H, t, J=7.24 Hz). m/z (ESI, +ve) 242.9 (M+H)+.

Provenance & Evidence