Sodium hydride → HCID 178430437, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 20A (0.6 g, 2.1 mmol) in N,N-dimethylformamide/tetrahydrofuran (1:4, 20 mL) were added sodium hydride (60% dispersion in mineral oil, 0.1 g, 2.5 mmol), tetrabutylammonium iodide (0.09, 0.23 mmol) and commercially available 4-(chloromethyl)-2-methylthiazole (Maybridge, 0.37 g, 2.5 mmol). The reaction mixture was stirred at 80° C. for 16 hours, cooled, diluted with ethyl acetate (20 mL) and quenched with saturated aqueous NaHCO3 (20 mL). The aqueous layer was extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with water (1×25 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280 ™ (SiO2, 0-50% ethyl acetate in hexanes) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.30 (s, 3 H), 2.63 (s, 3 H), 5.42 (s, 2 H), 7.34-7.39 (m, 2 H), 7.51 (s, 1 H), 7.52 (s, 1 H), 7.88 (t, J=1.5 Hz, 1 H); MS (ESI+) m/z 398 (M+H)+; Anal. Calculated for C16H13Cl2 N30S2 0.75H2O: C, 48.24; H, 3.29; N, 10.55. Found: C, 46.35; H, 3.46; N, 9.97.

Provenance & Evidence