Potassium Carbonate → 5-Bromo-3-(1-(2-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

5-Bromo-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine (Intermediate-1) (350 mg, 0.83 mmol) and 1-(2-fluorobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Intermediate-2) (301 mg, 0.99 mmol) were added to a solution of toluene/ethanol/water (5/5/2.5 ml) previously purged with argon (10 min). The reaction mixture was purged with argon for a further 15 mins, followed by the addition of potassium carbonate (230 mg, 1.6 mmol) and Pd(PPh3)4 (48 mg, 0.0415 mmol). 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 (20% ethyl acetate in hexane) afforded 285 mg (43.64% yield) of titled compound. MS: m/z=527.0 (M+1).

Provenance & Evidence