Potassium Fluoride → Tert-butyl 4-{3-[(3R)-3-({1-[5-(4-chloro-3-cyanophenyl)pyridin-3-yl]-3-methoxy-3-oxopropyl}carbamoyl)piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To 100.0 mg (0.16 mmol) tert-butyl 4-{3-[(3R)-3-{[1-(5-bromopyridin-3-yl)-3-methoxy-3-oxopropyl]carbamoyl}piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate (example 8c) in 4 ml toluene were added 3.8 mg tetrakis(triphenylphosphine)palladium(0), 35.7 mg (0.20 mmol) (4-chloro-3-cyano-phenyl)boronic acid in 1.0 ml ethanol and 29.6 mg (0.51 mmol) potassium fluoride in 1.0 ml water. The mixture was stirred at 100° C. for 6 hours, diluted with water and saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic phase was dried over sodium sulfate and concentrated in vacuum. Chromatography over 10 g silica gel (dichloromethane/ethanol 100/0-95/5-90/10) gave 44 mg (36%) Tert-butyl 4-{3-[(3R)-3-({1-[5-(4-chloro-3-cyanophenyl)pyridin-3-yl]-3-methoxy-3-oxopropyl}carbamoyl)piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate.

Provenance & Evidence