Potassium Phosphate, Tribasic → 4-(5-fluoro-2-methoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

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Reaction Conditions

Reaction Steps

A mixture of Example 248A (3.0 g, 9.78 mmol), (5-fluoro-2-methoxyphenyl)boronic acid (2.5 g, 14.6 mmol), phenylallylchloro(1,3-bis(diisopropylphenyl)-2-imidazol-2-yliden)palladium(II) (0.19 g, 0.29 mmol) and potassium phosphate (4.1 g, 19.6 mmol) in tetrahydrofuran (60 mL) and water (18 mL) was purged with nitrogen and heated at 60° C. for 3 hours. The mixture was treated with brine, extracted with ethyl acetate (three times) and the organic layer was dried over sodium sulfate. Filtration, concentration and purification by flash chromatography (Combi Flash Rf) (silica gel, 30% ethyl acetate in hexane) afforded the title compound. MS (ESI+) m/z 398 (M+H)+.

Provenance & Evidence