Tetrahydrofuran → 4-[1-Phenyl-1-(1-methylimidazol-4-yl)methylene]piperidine-1-carboxylic acid tert-butyl ester

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Reaction Conditions

Reaction Steps

A mixture of 4-(1-phenyl-1-iodo)methylene)-piperidine-1-carboxylic acid tert-butyl ester (0.112 g, 0.280 mmol), 4-tri-n-butylstannyl-1-methylimidazole (0.181 g, 0.486 mmol) Pd2(dba)3 (0.013 mg, 0.014 mmol) and tri-(2-furyl)phosphine (0.007 g, 0.031 mmol) in THF (4 mL) was heated at 70° C. in a sealed tube under Ar for 12 h. The mixture was cooled to rt, aqueous KF was added and the mixture was allowed to stir for 2 h. The resulting mixture was extracted with EtOAc (×3) and the combined organic layers were washed (H2O, brine), dried (Na2SO4) and concentrated in vacuo. The residue was purified by preparative HPLC (NH4OAc) to give the title compound (0.047 g, 47%) as an oil which was slightly contaminated with the starting stannane. This material was used in the following step without further purification.

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