Cesium carbonate → N-(1,6-dimethyl-3-(3-(pyrrolidin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)-1-methyl-1H-pyrazole-3-sulfonamide

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with 1-methyl-1H-pyrazole-3-sulfonamide (D94) (134 mg, 0.829 mmol), palladium(II) acetate (9.30 mg, 0.041 mmol), xantphos (47.9 mg, 0.083 mmol) and cesium carbonate (270 mg, 0.829 mmol). To this was added 4-chloro-1,6-dimethyl-3-(3-(pyrrolidin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine (D14) (135 mg, 0.414 mmol) dissolved in 1,4-dioxane (2.5 mL). The reaction mixture was heated at 150° C. in the microwave for 30 mins. The crude was purified on normal phase chromatography eluting with ethyl acetate in cyclohexane (0-80%) twice to give an impure material. The material was then dissolved in MeOH and passed through a SCX cartridge eluting with MeOH followed by 2M ammonia in MeOH to give a solid which was triturated with diethyl ether to give the title compound (38.7 mg). LCMS (A): m/z (M+H)+ 451, C23H26N6O2S requires 450 (acidic).

Provenance & Evidence