Cesium carbonate → {8-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethylsulfanyl]-chroman-5-yloxy}-acetic acid methyl ester

Participants

Reaction Steps

A solution of (8-mercapto-chroman-5-yloxy)-acetic acid methyl ester (410 mg, 1.6 mmol), 5-chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole (564 mg, 1.9 mmol) and cesium carbonate (787 mg, 2.4 mmol) in 15 ml anhydrous acetonitrile were stirred at 60° C. for 2.5 hours. The reaction was then cooled, filtered and concentrated in vacuo. Purification of the residue by flash column chromatography (gradient elution: 10% EtOAc/hexanes to 35% EtOAc/hexanes) afforded the title compound (95%). IR (thin film) cm−1: 1759; 400 MHz 1H NMR (DMSO-d6) δ 7.98 (d, 2H, J=8.3 Hz), 7.75 (d, 2H, J=8.3 Hz), 6.96 (d, 1H, J=8.6 Hz), 6.29 (d, 1H, J=8.6 Hz), 4.72 (s, 2H), 4.19 (s, 2H), 4.12 (t, 2H, J=5.1 Hz), 3.61 (s, 3H), 2.56 (t, 2H, J=6.6 Hz), 2.15 (s, 3H), 1.84 (m, 2H).; MS m/z 510 (M+1). Anal. Calc'd for C24H22F3N1O4S2 C, 56.57; H, 4.35; N, 2.75; found: C, 56.45; H, 4.27; N, 2.68.

Provenance & Evidence