Sodium Hydroxide → 4-[({[5-Fluoro-2-(4-fluorophenoxy)pyridin-3-YL]carbonyl}amino)methyl]benzoic acid

Participants

Reaction Steps

To a stirred solution of methyl 4-[({[5-fluoro-2-(4-fluorophenoxy)pyridin-3-yl]carbonyl}amino)methyl]benzoate (step 3, 407 mg, 1.02 mmol) in methanol (10 ml)_was added 2 N sodium hydroxide aqueous solution (2 mL). The reaction mixture was stirred at room temperature for 3 h and then evaporated. The residue was partitioned between ethyl acetate (100 mL) and 2 N hydrochloric acid (100 mL). The organic phase was separated and the aqueous phase was extracted with ethyl acetate (100 mL). The combined organic extracts were washed with brine (50 mL), dried (sodium_sulfate), and concentrated. The residual solids were recrystallized from ethyl acetate to afford 248 mg (64%) of the title compound as white solids: 1H-NMR (CDCl3) δ 8.40 (1H, dd, J=8.3, 3.1 Hz), 8.30 (1H, br.s), 8.09–8.04 (3H, m), 7.45 (2H, d, J=8.1 Hz), 7.17–7.06 (4H, m), 4.79 (2H, d, J=5.9 Hz); MS (EI) m/z 384 (M+), (ESI) m/z 385 (M+H)+, 383 (M−H)−.

Provenance & Evidence