Sodium hydride → HCID 11582332, compound

Participants

Reaction Steps

A solution of Example 65D (500 mg, 1.41 mmol) in DMF (7 mL) was treated with 60% sodium hydride (68 mg, 1.7 mmol) at room temperature, and the mixture was stirred at this temperature for 1 hour. Bromoethyl methyl ether (0.15 mL, 1.6 mmol) was then added, and the mixture was stirred overnight at room temperature. After this time, most of the DMF was evaporated in vacuo, then water (50 mL) was added. The resulting sticky residue was collected by filtration and was then chromatographed on silica gel (98:2 CH2Cl2—CH3OH) to afford the title compound, 131 mg (23%). 1H NMR (300 MHz, DMSO-d6) δ ppm 8.73 (s, 1H), 8.07 (s, 1H), 7.69 (d, J=6.44 Hz, 1H), 7.32 (dd, J=15.09, 7.63 Hz, 1H), 7.18-7.26 (m, 2H), 6.71-6.79 (m, 2H), 6.61 (dd, J=10.85, 2.71 Hz, 1H), 4.96 (m, 1H), 4.51 (t, J=5.43 Hz, 2H), 3.75 (t, J=5.43 Hz, 2H), 3.18 (s, 3H), 2.20 (dd, J=13.39, 6.27 Hz, 1H), 1.78 (dd, J=13.05, 11.02 Hz, 1H), 1.41 (s, 3H), 1.30 (s, 3H). MS (ESI+) m/z 413 (M+H), 435 (M+Na).

Provenance & Evidence