Methyl iodide → HCID 11113517, compound

Participants

Reaction Steps

4-(6-Chlorobenzo[b]thiophene-2-sulfonyl)-1-(1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one (0.59 g, 1.28 mmol), EXAMPLE 214, is dissolved in anhydrous DMF (30 ml), cooled in an ice bath, treated with 60% sodium hydride (0.061 g, 1.53 mmol) and stirred at room temperature for 30 minutes. The solution is treated with methyl iodide (83 mL, 1.33 mmol) and warmed to room temperature over 4 hours. The reaction is quenched with ammonium chloride solution, diluted with ethyl acetate and separated. The organic layer is washed with brine (3×), dried (Na2SO4) and concentrated. The residue is purified by flash chromatography (5-10% MeOH/CH2Cl2) to provide the title compound (0.31 g, 0.65 mmol). 1H NMR (CD3OD, 300 MHz) δ8.55 (d, 1H), 7.99 (dd, 1H), 7.82 (m, 3H), 7.49 (dd, 1H), 7.43 (d, 1H), 6.55 (s, 1H), 4.75 (s, 2H), 3.96 (s, 2H), 3.52 (m, 4H), 3.86 (s, 3H), 3.49 (s, 3H). Ion Spray MS, [M+H]+=477.

Provenance & Evidence