Sodium Carbonate → HCID 57502422, compound

Participants

Reaction Conditions

Reaction Steps

To a degassed (sparging with argon for 5 minutes), stirred solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)-pyrazole-1-carboxylic acid tert-butyl ester (1.31 g, 4.45 mmol) and 5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (1.00 g, 2.97 mmol) in dioxane (12.0 ml) was added Pd(Ph3P)4 (0.171 g, 0.148 mmol), followed by a degassed aqueous solution of sodium carbonate (4.45 ml, 8.90 mmol). The reaction mixture was stirred under nitrogen at 100° C. for 1 hour. The reaction mixture was cooled to room temperature and partitioned between EtOAc (50 mL) and saturated aqueous ammonium chloride (50 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated to a crude residue. The residue was purified by silica gel chromatography (EtOAc/Hexanes gradient) to afford 1-(phenylsulfonyl)-5-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine as a yellow solid. LRMS (ESI) calculated for C16H12N4O2S [M+H]+, 325.1; found 325.0.

Provenance & Evidence