Benzyl Bromide → 4-{2-[1-Benzyl-3-(1-tert-butoxycarbonylmethyl-piperidin-4-yl)-1H-indazol-6-yl]-(E)-vinyl}-piperidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

A solution of 4{-2-[3-(1-tert-butoxycarbonylmethyl-piperidin-4-yl)-1H-indazol-6-yl]-(E)-vinyl}-piperidine-1-carboxylic acid tert-butyl ester (152 mg, 0.29 mmol) in dry DMF (2 ml) under nitrogen was treated with sodium hydride (5 mg of a 60% dispersion in oil, 0.37 mmol) and stirred at +23° for 20 min. The solution was treated with a solution of benzyl bromide in dry DMF (0.1 ml of 3.14M solution, 0.314 mmol; Aldrich). The resulting mixture was stirred at +23° for 24 h and concentrated in vacuo. The residue was dissolved in dichloromethane (100 ml) and the solution washed with water (2×25 ml). The dried (MgSO4) organic layer was concentrated in vacuo onto silica (Merck 9385); purification by flash chromatography eluting with ether--cyclohexane (1:1) gave the title compound as a white foam (102 mg).

Provenance & Evidence