Water → 4-((3-(2-(2,4-difluorophenoxy)-5-nitrophenyl)-7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-5-yl)methyl)morpholine

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Reaction Steps

A mixture of Example 182B (110 mg, 0.224 mmol), potassium trifluoro(morpholinomethyl)borate (55.7 mg, 0.269 mmol), palladium (II) acetate (3.02 mg, 0.013 mmol), dicyclohexyl(2′,4′,6′-triisopropyl-[1′,1′-biphenyl]-2-yl)phosphine (12.83 mg, 0.027 mmol), and Cs2CO3 (219 mg, 0.673 mmol) in 4 mL dioxane-water (9:1) was heated under nitrogen in Biotage Initiator microwave oven at 150° C. for 45 minutes. Water was added, extracted with ethyl acetate (2×), washed with water (2×), saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate, filtered. The filtrate was concentrated, and the residue was purified by column chromatography on silica gel with a gradient of 0-8% methanol in dichloromethane to give the title compound (60 mg, 0.118 mmol, 52.4% yield).

Provenance & Evidence