Sodium Carbonate → 4-fluoro-3-(6-(1-(methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)aniline

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Reaction Conditions

Reaction Steps

To a solution of Example 29A (1.10 g, 2.429 mmol), 4-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (749 mg, 3.16 mmol), and bis(triphenylphosphine)palladium(II) dichloride (170 mg, 0.243 mmol) in 7/2/3 1,2-dimethyoxyethane/ethanol/water (30 mL) was added sodium carbonate (3.64 mL, 7.29 mmol). The mixture was heated at 90° C. for 1 hour, cooled and diluted with 50 mL ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate, water, and brine, dried over magnesium sulfate, filtered, and concentrated. The residue was dissolved in 30 mL dioxane, treated with 6M sodium hydroxide (4.05 mL, 24.29 mmol), heated at 100° C. for 1 hour, cooled and diluted with 50 mL ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate, water and brine, dried over magnesium sulfate, filtered, and concentrated. The residue was triturated with ethyl acetate to give the title compound. MS (ESI+) m/z 388.2 (M+H)+.

Provenance & Evidence