Dimethylformamide → 5-chloro-2-(1-methyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A solution in a microwave vial of 4,5-dichloro-2-(1-methyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (Example 113C) (300 mg, 0.712 mmol) in anhydrous N,N-dimethylformamide (4 mL) was degassed by nitrogen sparge for about 20 minutes. The solution was treated with zinc cyanide (167 mg, 1.424 mmol) and tetrakis(triphenylphosphine)palladium (82 mg, 0.071 mmol). The reaction was degassed and back-filled with nitrogen, and heated in a Biotage Initiator microwave for 60 minutes at 160° C. The reaction was treated with additional zinc cyanide (83 mg, 0.712 mmol) and tetrakis(triphenylphosphine)palladium (41 mg, 0.035 mmol), and heated to 160° C. for 30 minutes by microwave irradiation. The reaction was diluted with water and ethyl acetate, and the layers were separated. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 25 to 40% ethyl acetate in hexanes, to provide the title compound. MS ESI(+) m/z 412.4 [M+H]+.

Provenance & Evidence