Acetic Acid → HCID 54575574, compound

Participants

Reaction Steps

To a solution of 5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazole-4-carbaldehyde (intermediate B4:1, 0.02 g, 0.06 mmol) in DCE was added methyl 4-aminobenzoate (0.01 g, 0.06 mmol), acetic acid (3.4 ul, 0.06 mmol) and NaBH(OAc)3 (0.015 g, 0.07 mmol). After Stirring at rt overnight, a drop of water was added to the reaction and purified by reverse phase HPLC to give methyl 4-[({5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazol-4-yl}methyl)amino]benzoate. 1H NMR (400 MHz, CDCl3) δ 8.35 (d, J=2.5 Hz, 1H), 8.05 (m, 2H), 737 (d, J=8.8 Hz, 2H), 7.44 (dd, J=8.4, 2.5 Hz, 1H), 7.14 (m, 2H), 6.90 (d, J=8.4 Hz, 1H), 6.61 (d, 3=8.8 Hz, 2H), 4.43 (s, 2H), 3.84 (s, 3H); HRMS exact mass calc for C23H17ClFN3O3S [M+H]: 470.0736; observed: 470.0734.

Provenance & Evidence