Methyl chloroformate → HCID 68821818, compound

Participants

Reaction Steps

The product from Example 3 (500 mg, 1.45 mmol), methyl chloroformate (0.43 mL, 5.56 mmol), and K2CO3 (1.15 g, 8.33 mmol) were heated in DME (8 mL) at 65° C. for 24 hours. The mixture was allowed to cool to room temperature, concentrated under reduced pressure, and the residue was taken up in ethyl acetate (50 mL). The ethyl acetate was washed with H2O (3×15 mL) and brine (15 mL), dried over Na2SO4, filtered, and the filtrate concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluant gradient from 99:1 CH2Cl2:CH3OH to 95:5 CH2Cl2:CH3OH) to provide the title compound as a solid. 1H NMR (300 MHz, DMSO-d6) δ 10.24 (s, 1H), 9.15 (s, 1H), 8.53 (dd, J=4.5 Hz, 1.6 Hz, 1H), 8.02-8.05 (m, 2H), 7.88 (dd, J=8.1 Hz, 1.4 Hz, 1H), 7.70-7.77 (m, 4H), 7.35-7.46 (m, 3H), 3.55 (s, 3H), 1.29 (s, 9H); MS (ESI+) m/z 404 (M+H)+.

Provenance & Evidence