Reaktion #271
ord-0dc07c6e11344615900455301860696c
Reaktionsgleichung
Lösungsmittel
Reaktionsbedingungen
Vorschrift
2-(2,5-dichloropyridin-4-ylamino)-N-methoxybenzamide (200 mg, 0.64 mmol), 1-isopropyl-3-methyl-1H-pyrazol-5-amine (178 mg, 1.28 mmol) and cesium carbonate (313 mg, 0.96 mmol) were suspended in 1,4-dioxane (3 mL). Nitrogen was bubbled through mixture for 10 minutes. (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (27.8 mg, 0.05 mmol) and diacetoxypalladium (7.19 mg, 0.03 mmol) were added and tube was sealed. Mixture was stirred at reflux overnight => _incomplete reaction_. Reaction was heated for a further 7 hours => _no evolution_. More Pd(OAc)2 and Xantphos were added, mixture was degassed with nitrogen and heated at reflux overnight => _complete_. Reaction was allowed to cool to room temperature, filtered, washed with CH2Cl2/MeOH (9/1, 10 mL) and concentrated to dryness. The crude product was purified by flash chromatography (dry loading) on silica gel eluting with 1 to 5% methanol in dichloromethane. The solvent was evaporated to dryness to afford 2-(5-chloro-2-(1-isopropyl-3-methyl-1H-pyrazol-5-ylamino)pyridin-4-ylamino)-N-methoxybenzamide (90 mg, 33.9 %) as a pink foam.