Benzophenone imine → 5-(Cyclopropylmethoxy)pyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-5-(cyclopropylmethoxy)pyridine (5.65 g), tris(dibenzylideneacetone)dipalladium(0) (454 mg), 1,1′-binaphthalene-2,2′-diylbis(diphenylphosphine) (925 mg), 1,1-diphenylmethanimine (5.42 g), sodium t-butoxide (3.33 g) and toluene (50 mL) was stirred at 80° C. for 3 hr under an argon atmosphere. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with THF (15 mL). 1M Hydrochloric acid (15 mL) was added thereto, and the mixture was stirred at room temperature for 30 min. 6M Hydrochloric acid (6 mL) was added thereto, and the organic layer was separated from the aqueous layer. The separated organic layer was extracted with 1M hydrochloric acid. The combined aqueous layer was neutralized with 8M aqueous sodium hydroxide solution, and extracted twice with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate), and recrystallized (hexane/diethyl ether) to give the title compound as colorless crystals (3.67 g).

Provenance & Evidence