Water → HCID 131734682, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of compound 42a (616 mg, 2.10 mmol) in DMF (5 mL) was added K2CO3 (1.0 g, 7.2 mmol) and SEM-Cl (563 μL, 3.17 mmol). The resulting mixture was stirred at 75° C. for 4 h, allowed to cool to rt and treated with water (20 mL). The reaction mixture was then extracted with DCM (3×20 mL). The combined DCM layers were dried over Na2SO4, filtered, and concentrated to obtain a residue which was purified by flash column chromatography on silica gel (0-50% EtOAc/hexanes) to obtain compound 42b. 1H-NMR (400 MHz, CDCl3) δ (ppm): 7.99 (d, J=2.0 Hz, 1H), 7.74 (dd, J=9.1, 2.5 Hz, 1H), 7.51 (d, J=9.1 Hz, 1H), 5.42 (s, 2H), 3.71-3.77 (m, 2H), 3.35 (s, 3H), 0.91-0.98 (m, 2H), 0.01 (s, 9H).

Provenance & Evidence