Potassium Carbonate → 1-tert-Butyl-5-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(5-methoxy-2-pyrazol-1-yl-phenyl)-1H-benzimidazole

Participants

Reaction Conditions

Reaction Steps

In a microwave vial are combined 1-tert-butyl-2-(5-methoxy-2-pyrazol-1-yl-phenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazole (285 mg, 0.60 mmol), 5-bromo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine (100 mg, 0.50 mmol), potassium carbonate (140 mg, 1.0 mmol), and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (53 mg, 0.08 mmol) in toluene (3.0 mL) and water (0.30 mL). The reaction vial is sealed and stirred at 100° C. for 4 hours in an oil bath. After this time the reaction is cooled and poured into water. The product is extracted into EtOAc (2×). The combined organics are dried (MgSO4), filtered and concentrated. Purification via flash chromatography (12 g silica gel, 0-5% MeOH/CH2Cl2) affords the title compound (40 mg, 17%). LCMS (ESMS): m/z 465.20 (M++1)

Provenance & Evidence