Methyl iodide → Ammonium Hydroxide

Participants

Reaction Steps

A solution of Example 44 (0.041 g, 0.1 mmol) in DMF (1.0 mL) at 0° C. was treated with 60% NaH in mineral oil (4 mg, 0.1 mmol), stirred for 15 minutes, treated with a 0° C. solution of iodomethane (15.6 mg, 0.11 mmol) in DMF (0.5 mL), stirred for 30 minutes, diluted with ethyl acetate, washed with water and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 10:1:0.1 EtOAc:MeOH:NH4OH to provide the desired product. MS (APCI) m/z 431 (M+H)+; 1H NMR(MeOH-d4) δ 8.92 (s, 1H), 8.19 (s, 1H), 7.73 (d, 2H), 7.50-7.41 (m, 5H), 7.32 (d, 1H), 7.24 (s, 1H), 6.67 (s, 1H), 5.86 (s, 1H), 4.52 (d, 1H), 4.40 (d, 1H), 3.79 (s, 3H), 3.67 (s, 3H).

Provenance & Evidence