Potassium Carbonate → Tert-butyl 2-({1-[4-(5-cyanopyridin-2-yl)phenyl]cyclopropyl}carbonyl)hydrazinecarboxylate

Participants

Reaction Steps

A mixed solution of the compound (100 g, 249 mmol) obtained in Example 60-1), 2-chloro-5-cyanopyridine (44.8 g, 323 mmol), potassium carbonate (68.7 g, 497 mmol), and tetrakis(triphenylphosphine)palladium (14.4 g, 12.4 mmol) in 1,2-dimethoxyethane (800 mL) and water (200 mL) was stirred at 100° C. for 8 h, then at 80° C. for 14 h, and further at 100° C. for 5 h. The reaction mixture was cooled to room temperature, insoluble substances were filtered off, dichloromethane was added to the filtrate, and the organic layer was washed with saturated aqueous sodium hydrogencarbonate and saturated sodium chloride solution in this order. The solvent was distilled off under reduced pressure, and the residue was washed with dichloromethane and hexane and then purified by silica gel column chromatography (ethyl acetate:methanol=1:1) to obtain the title compound (24.1 g, 26%) as a white solid.

Provenance & Evidence