Potassium Phosphate, Tribasic → tert-butyl (3R)-3-({[3-(pyridin-4-yl)-1-trityl-1H-indazol-5-yl]carbonyl}amino)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A flask was charged with tert-butyl (3R)-3-{[(3-bromo-1-trityl-1H-indazol-5-yl)carbonyl]amino}piperidine-1-carboxylate (4.00 g, 6.01 mmoles), potassium phosphate (2.05 g, 9.66 mmoles) and 1,1′-Bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (160.0 mg, 0.219 mmoles). The flask was put under an atmosphere of argon (3× vacuum/argon cycle) and degassed dioxane (20 mL) and water (5 mL) were injected. The reaction was heated to 80° C. for 16 hours and was then allowed to cool to ambient temperature. The resulting solution was poured into water (100 mL) and the aqueous emulsion was washed three times with chloroform/isopropanol (4:1, 50 mL portions). The combined organic washings were dried over sodium sulfate, filtered and concentrated to dryness. Flash chromatography (gradient 0-15% dichloromethane/methanol) to yield tert-butyl (3R)-3-({[3-(pyridin-4-yl)-1-trityl-1H-indazol-5-yl]carbonyl}amino)piperidine-1-carboxylate as a white solid (3.79 g, 95%).

Provenance & Evidence