Methyl iodide → HCID 66665424, compound

Participants

Reaction Steps

A suspension of sodium hydride (61.1 mg of a 60% mixture in mineral oil, 1.528 mmol) in dry DMF (5 ml) under N2 was treated with a solution of rac-ethyl 6-(6,7-diphenyl-1,2,3,4-tetrahydro-1,8-naphthyridin-2-yl)hexanoate (step 3) (131 mg, 0.306 mmol) in DMF (5 ml). After 30 mins at room temperature iodomethane (0.096 ml, 1.528 mmol) was added and stirring continued for 5 h. The mixture was partitioned between DCM (50 ml) and water (50 ml) and the aqueous portion was separated and extracted with DCM (3×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. Purification of the crude product by chromatography on silica eluting with 0-30% EtOAc in iso-hexane afforded a mixture of the title products as a colourless oil;

Provenance & Evidence