Cesium carbonate → (R)-1-(4-(hydroxymethyl)-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea

Participants

Reaction Conditions

Reaction Steps

Chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′-4′-6′-tri-i-propyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl]palladium(ii) (67.5 mg, 0.084 mmol), (6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)methanol (35B, 385 mg, 0.844 mmol), cesium carbonate (825 mg, 2.53 mmol) and (R)-1-(1-phenylethyl)urea (277 mg, 1.689 mmol) were taken up in dioxane (5 ml) in a 1.5 mL microwave vial and the vial was evacuated and back-filled with N2 (×3). The reaction mixture was stirred at 90° C. for 2 hours. The crude reaction mixture was diluted with DCM and filtered through syringe filter. The filtrate was concentrated, and purified on 80 g Redsep gold silica gel 5-25% DCM/EtOAc to provide (R)-1-(4-(hydroxymethyl)-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea. MS: [M+H]+ m/z 584.

Provenance & Evidence