Methyl iodide → HCID 86592635, compound

Participants

Reaction Conditions

Reaction Steps

6-Methoxy-4-(piperidin-4-ylamino)-chromen-2-one and indole-5-carboxaldehyde were allowed to react under reductive alkylation conditions to give a crude beige product. After trituration of the crude product with hot ethyl acetate, filtration and concentration, the resulting partially-purified white powder was carried on to the subsequent alkylation step. A solution of this material (202 mg, 0.5 mmol) in 2 mL DMF under nitrogen at 0° C., was treated with NaH (60% dispersion in mineral oil, 50 mg, 12.5 mmol). After 45 minutes, methyl iodide (33 uL, 0.525 mmol) was added via syringe. The reaction was stirred at 0° C. for two hours, and then allowed to warm to room temperature and stirred overnight. After 17 hours, the reaction was quenched by slow addition of distilled water, diluted with CH2Cl2/MeOH (95:5), washed with distilled water, dried (Na2SO4) and concentrated to give a yellow oil. Purification by flash silica gel chromatography (0 to 5% MeOH in CH2Cl2) gave the titled compound as a yellow foam (80 mg). 1H NMR (300 MHz, ppm, DMSO-d6) δ 1.57-1.71 (m, 2H), 1.86-1.96 (m, 2H), 2.04-2.15 (m, 2H), 2.73 (m, 2H), 3.46-3.58 (m, 3H), 3.77 (s, 3H), 3.83 (s, 3H), 5.21 (s, 1H), 6.38 (d, J=3.1 Hz, 1H), 7.10-7.23 (m, 3H), 7.29 (d, J=3.1 Hz, 1H), 7.37 (d, J=8.4 Hz, 1H), 7.45 (s, 1H), 7.63 (d, J=2.8 Hz, 1H) MS(ESI) 418 (M+H), 416 (M−H).

Provenance & Evidence