2-Bromopyridine → 8-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-8-methyl-3-[1-(4-pyridin-2-ylphenyl)cyclopropyl]-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine

Participants

Reaction Steps

A solution of the compound (555 mg, 1.0 mmol) obtained in Example 16-5), 2-bromopyridine (243 mg, 2 mmol), tetrakis(triphenylphosphine)palladium(0) (231 mg, 0.2 mmol), and potassium carbonate (276 mg, 2 mmol) in dimethoxyethane (4 mL) and water (1 mL) was stirred at 100° C. for 30 min under microwave irradiation. The reaction mixture was cooled to room temperature and purified by silica gel chromatography (Isco Combiflash, 40 g, methanol:ethyl acetate=0:100 to 20:80, gradient) to obtain the title compound (346 mg, 68%) as a brown solid.

Provenance & Evidence