4-Hydroxypyrrolidine → 1-(6-Chloro-2-methoxypyridin-3-yl)pyrrolidin-3-ol

Participants

Reaction Conditions

Reaction Steps

A vial was charged 3-bromo-6-chloro-2-methoxypyridine(0.50 g, 2.2 mmol), pyrrolidin-3-ol (0.39 g, 4.5 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.10 g, 0.10 mmol), Xantphos (0.13 g, 0.20 mmol), sodium tertbutoxide (0.32 g, 3.4 mmol) and toluene (5 mL). The mixture was purged with nitrogen then sealed. The mixture was heated to 100° C. overnight. The mixture was cooled to room temperature, filtered and diluted with 15 mL of water. The solution was extracted with ethyl acetate (10 mL×3). The organic layers were combined, dried over sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel chromatography to give the title compound (29.5 mg, 5.7%) as light brown solid.

Provenance & Evidence