tert-butyl (3R)-3-aminopiperidine-1-carboxylate → HCID 86702326, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-chloro-3-(2-methoxypyridin-3-yl)imidazo[1,2-b]pyridazine (Preparation 2, 0.15 g, 0.58 mmol), tert-butyl (3R)-3-aminopiperidine-1-carboxylate (0.23 g, 1.15 mmol), 2′-(dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (0.03 g, 0.09 mmol), sodium tert-butoxide (0.08 g, 0.81 mmol) and toluene (4 mL) in a Schlenk vial was subjected to three cycles of evacuation backfilling with argon. Tris(dibenzylidene acetone)dipalladium(0) (0.04 g, 0.04 mmol) was then added and the resulting mixture was subjected to three further cycles of evacuation backfilling before being heated at 110° C. for 20 hours. Subsequently, the reaction was cooled down, filtered through Celite® eluting with ethyl acetate and dichloromethane, and the filtrate was evaporated to dryness. The crude was purified by flash chromatography (1:1 hexanes/ethyl acetate to 100% ethyl acetate) to give the title compound (0.105 g, 42%) as a solid.

Provenance & Evidence