Sulfanilamide → 4-({4-[(2,6-Dimethylpyridin-3-yl)oxy]pyridin-2-yl}amino)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

XANTPHOS (2.466 g, 4.26 mmol) was added to 3-(2-chloropyridin-4-yloxy)-2,6-dimethylpyridine (10g, 42.61 mmol), Sulfanilamide (9.54 g, 55.39 mmol) and CESIUM CARBONATE (20.83 g, 63.92 mmol) in DMA (200 ml) at 20ºC. Nitrogen was bubbled through the reaction mixture for 1 hour then PALLADIUM(II) ACETATE (0.670 g, 2.98 mmol) added. The suspension was stirred at 130 °C for 3 hours. The reaction mixture was filtered then evaporated to dryness. The residue was triturated with water (150 mL) and filtered to give crude product as a cream solid - 90% pure. The crude solid was triturated with hot acetonitrile (300 mL) and filtered to afford crude product as a cream solid - 98% by LCMS. This was combined with the product from EN02084-31 and dissolved in boiling acetonitrile (approx 1 L). The solution was concentrated to 500 mL and cooled to ice bath temperature with stirring. A precipitate formed which and the suspension was stirred at room temperature overnight. The solid was filtered to afford 4-(4-(2,6-dimethylpyridin-3-yloxy)pyridin-2-ylamino)benzenesulfonamide (12.00 g, 76 %) as a cream solid.

Provenance & Evidence