2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1-(5-(5-chloro-2-(1-methyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)cyclobutanamine

Participants

Reaction Steps

A solution of 1-(5-(5-chloro-2-(1-methyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)-N-(4-methoxybenzyl)cyclobutanamine (500 mg, 0.758 mmol) (Example 112D) in anhydrous dichloromethane (20 mL) and water (1.0 mL) was treated with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (224 mg, 0.986 mmol) and stirred for 20 minutes at ambient temperature. Additional 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (50 mg, 0.220 mmol) was added to the mixture, and the reaction stirred one hour at ambient temperature. The reaction was quenched with saturated sodium bicarbonate, and layers were separated. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 100% ethyl acetate to 5% methanol in ethyl acetate, to provide the title compound. MS ESI(+) m/z 539.1 [M+H]+.

Provenance & Evidence