Dimethylformamide → HCID 18800617, compound

Participants

Reaction Steps

To a stirred solution of DMF (15 mL) and POCl3 (256 mg, 1.7 mmol) at 0° C. was added 1-(4-benzylpiperidine-carbonyl)methyl-5-cyanoindole (199 mg, 0.56 mmol). After stirring 3 h, the reaction was quenched with 2N sodium hydroxide and stirred for 30 min. It was then extracted with chloroform, dried with sodium sulfate, filtered and concentrated in vacuo to afford product. LRMS (M+H)+ 386. The product was then refluxed in the presence of triphenyl phosphonium(methylenecarbomethoxy)ylide in THF under a nitrogen atmosphere for 18 h. The reaction was concentrated in vacuo and the residue purified via silica gel chromatography using 7% MeOH/CHCl3 as the eluant to afford 140 mg of product.

Provenance & Evidence