Picolyl chloride hydrochloride → HCID 11353926, compound

Participants

Reaction Steps

2-Picolyl chloride hydrochloride (164 mg, 1 mmol) was added to potassium hydride (228 mg of 40% KH, 2 mmol, in mineral oil, washed with hexanes) in 5 mL of dry N,N-dimethylformamide at room temperature. Ethyl 4-{2-[1-benzhydryl-5-chloro-2-(hydroxymethyl)-1H-indol-3-yl]ethoxy}benzoate (140 mg, 0.25 mmol) in 3 mL of N,N-dimethylformamide was added via syringe. After stirring at room temperature for 2 hours, the reaction was quenched with iced water, extracted with CH2Cl2, dried over magnesium sulfate and purified by preparative thin layer chromatography (20% methanol/CH2Cl2 as the developing solvents) to yield 16 mg (11%) of the desired product as a pale yellow solid. m/z (M−1) 600.9.

Provenance & Evidence