Sodium Carbonate → N-(3-(1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide

Participants

Reaction Conditions

Reaction Steps

5-bromo-1H-pyrrolo[2,3-b]pyridine (1 g, 5 mmol) and N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide (intermediate 3) (1.6 g, 5 mmol) were added to a solution of toluene/ethanol/water (6/6/5 ml) previously purged with argon (10 min). The reaction mixture was purged with argon for a further 15 mins, followed by the addition of sodium carbonate (1.64 g, 15 mmol) and PdCl2(dppf) (181 mg, 0.2 mmol) and DME/water (10/5 ml). The resulting mixture was heated to reflux at 80° C. overnight. The reaction was monitored by TLC (50% ethylacetate in hexane). The reaction mixture was cooled and diluted with ethyl acetate (50 ml) and washed with water (2×50 ml). The organic layer was dried over Na2SO4, and concentrated under reduced pressure to afford crude product. Purification by column chromatography on silica gel (40% ethyl acetate in hexane) afforded 800 mg (57% yield) MS: m/z=287.9 (M+1).

Provenance & Evidence