Triethylamine → HCID 117771250, compound

Participants

Reaction Steps

To a solution of 3-(benzyloxy)-6-bromopicolinic acid (1.90 g, 6.2 mmol), HATU (4.69 g, 12.4 mmol) and Et3N (0.5 mL) in DMF (20 mL) was added 4-fluorobenzylamine (2.30 g, 18.5 mmol) dropwise. The mixture was stirred at room temperature overnight. Then it was concentrated and extracted with EtOAc. The combined organic phase was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash gel chromatography (PE:EtOAc=2:1) to afford the product of 3-(benzyloxy)-6-bromo-N-(4-fluorobenzyl)picolinamide (2 g, yield: 77.8%). 1H-NMR (CDCl3, 400 MHz) δ 7.84 (s, 1H), 7.42˜7.45 (m, 3H), 7.23˜7.37 (m, 6H), 6.97 (t, J=8.8 Hz, 2H), 5.21 (s, 2H), 4.57 (d, J=6.0 Hz, 2H). MS (M+H)+: 415/417.

Provenance & Evidence