Hydrochloric Acid → HCID 58317731, compound

Participants

Reaction Steps

To a mixture of 2,6-dichloro-4-((3,5-dimethoxybenzylimino)methyl)-5-fluoronicotinic acid (5.8 g, 25.3 mmol) in THF (120 mL) was added methyl-lithium (60.0 mL, 126.6 mmol) drop wise at −78° C. After the addition was completed, the mixture was stirred for an additional 2 h. The reaction mixture was acidified with 1N HCl to pH 7 and THF was removed under reduced pressure. The mixture was extracted with EtOAc, washed with brine, dried over anhydrous Na2SO4, and purified by silica gel chromatography eluting with PE-EtOAc (5:1) to give the title compound as a white solid (0.93 g, 16%). 1H-NMR (CDCl3, 400 MHz) δ 1.58 (d, J=6.8 Hz, 3 H), 3.79 (s, 3 H), 3.84 (s, 3 H), 4.35 (d, J=14.4 Hz, 1 H), 4.52 (q, J=6.8 Hz, 1 H), 5.07 (d, J=14.4 Hz, 1 H), 6.43-6.45 (m, 2 H), 7.28 (d, J=9.2 Hz, 1 H). [M+H] calc'd for C17H15Cl2FN2O3, 386; found, 385.

Provenance & Evidence