Methyl Glycolate → [5-(4-Fluorophenylcarbamoyl)Pyridin-2-Yloxy]Acetic Acid Methyl Ester

Participants

Reaction Conditions

Reaction Steps

A suspension of 6-bromo-N-(4-fluorophenyl)nicotinamide (1.0 g, 3.4 mmol), methyl glycolate (1.6 mL, 19 mmol), and potassium tert-butoxide (1.5 g, 13.6 mmol) in THF (10 mL) was heated in a sealed tube at 70° C. After 3 h the reaction mixture was poured onto ice and the solids isolated by filtration. Purification on silica gel by column chromatography using 30% ethyl acetate in hexanes gave 0.68 g (65%) of the titled product as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 10.30 (s 1H), 8.66 (m, 1H), 8.22 (m, 1H), 7.73 (m, 2H), 7.16 (m, 2H), 7.04 (m, 1H), 4.98 (s, 2H), 3.65 (s, 3H); MS (EI) m/z 303.13 (M−H)−.

Provenance & Evidence