Sodium Iodide → 3-ethyl-6-methyl-5-(pyrrol-1-yl)-1H-pyridin-2-one

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-ethyl-2-methoxy-6-methyl-5-pyrrol-1-yl-pyridine (68 mg, 0.315 mmol) and sodium iodide (141 mg, 0.94 mmol) under a N2 atmosphere is added anhydrous acetonitrile (4 mL) followed by dropwise addition of chlorotrimethylsilane (118 μL, 0.940 mmol). The reaction mixture is stirred at 65° C. under nitrogen for 17 hr. The reaction mixture is allowed to cool, diluted with water and extracted with three portions of dichloromethane. The combined extracts are dried over magnesium sulfate and evaporated to leave an orange residue. The crude product is purified by flash chromatography on a 5-gram silica gel cartridge by elution with dichloromethane:methanol (49:1). Clean fractions containing the product are combined and evaporated to give 3-ethyl-6-methyl-5-(pyrrol-1-yl)-1H-pyridin-2-one (59 mg, 93% yield) as a white solid. This material (49 mg) is dissolved in dichloromethane (2 mL) and treated with ethereal hydrochloric acid (2.0M, 0.49 mL). The solution is stirred for 1.5 hr and then evaporated to give 3-ethyl-6-methyl-5-pyrrol-1-yl-1H-pyridin-2-one hydrochloride (54 mg) as an off-white solid. LC/MS: RT: 2.70 min, MS: m/e=203 (M+H); 1H NMR (δ ppm): 11.75 (1H, s), 7.16 (1H, s), 6.80 (2H, t), 6.16 (2H, t), 2.38 (2H, q), 1.97 (3H, s), 1.08 (3H, t).

Provenance & Evidence