Cesium carbonate → Methyl 6-(((4-fluorobenzyl)amino)methyl)picolinate

Participants

Reaction Steps

To a solution of methyl 6-((methylsulfonyloxy)methyl)picolinate (0.4 g, 1.63 mmol) in CH3CN (15 mL) were added 4-fluorobenzylamine (0.75 mL, 6.52 mmol) and Cs2CO3 (0.8 g, 2.45 mmol). The reaction mixture was stirred at rt for 4 h, filtered and the filtrate solution was concentrated in vacuo. The residue was purified by preparative HPLC. Fractions containing the desired product were combined and concentrated to give the desired compound (140 mg, 31%) as an oil. 1H NMR (CDCl3) δ 8.02 (d, J=8.0 Hz, 1H), 7.81 (t, J=8.0 Hz, 1H), 7.59 (d, J=8.0 Hz, 1H), 7.35-7.31 (m, 2H), 7.04-6.99 (m, 2H), 4.02 (s, 2H), 3.99 (s, 3H), 3.82 (s, 2H). MS (ESI): 275.1 (M+H)+.

Provenance & Evidence