1,4-Dioxane → (R)-4-((1-cyclobutylethyl)amino)-7-methyl-3-(4-(trifluoromethyl)benzyl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile

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To a vial containing (R)-7-bromo-4-((1-cyclobutylethyl)amino)-3-(4-(trifluoromethyl)benzyl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile (65 mg, 0.14 mmol), methylboronic acid (16.3 mg, 0.3 mmol), 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride-chloroform adduct (11.1 mg, 0.014 mmol) and potassium phosphate (87 mg, 0.41 mmol) was added 1,4-dioxane (800 ul) and water (200 uL). The vial was evacuated and refilled with Ar (3×). The solution was heated to 120° C. for 10 minutes under microwave irradiation. The mixture was cooled to room temperature and quenched with saturated sodium bicarbonate and ethyl acetate. The organic layer was collected and concentrated. The residue was dissolved in DCM and purified by silica gel chromatography (0-100% ethyl acetate/hexanes, linear gradient) to give (R)-4-((1-cyclobutylethyl)amino)-7-methyl-3-(4-(trifluoromethyl)benzyl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile. MS ESI calc'd for C22H22F3N5 [M+H]+ 414. found 414.

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