Cesium fluoride → 3-chloro-N-(3-(3-(pyrrolidin-1-yl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

A mixture of N-[3-bromo-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-3-chlorobenzenesulfonamide (D4) (233 mg, 0.451 mmol), [3-(1-pyrrolidinyl)phenyl]boronic acid (129 mg, 0.676 mmol), cesium fluoride (205 mg, 1.352 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (36.8 mg, 0.045 mmol) in DME (5.706 mL) was heated in a microwave at 120° C. for 30 minutes. Additional 3-(1-pyrrolidinyl)phenyl]boronic acid (129 mg, 0.676 mmol), cesium fluoride (68.3 mg) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (36.8 mg, 0.045 mmol) were added into the reaction mixture and heated in a microwave at 120° C. for 1 hour. The reaction mixture was partitioned between aqueous saturated NaHCO3 solution and ethyl acetate. The aqueous phase was separated and extracted with ethyl acetate (thrice). The organic extracts were combined, dried over phase separator. The residue was purified on silica gel, eluting with a gradient of 0-40% ethyl acetate in cyclohexane). The appropriate fractions were combined and evaporated to dryness to afford the title compound (128.1 mg). LCMS (A): m/z (M+H)+ 583, C29H35ClN4O3SSi requires 582 (acidic).

Provenance & Evidence