Reaktion #292
ord-0f54af454e1c49e3950d93f112c4112b
Reaktionsgleichung
Lösungsmittel
Reaktionsbedingungen
Vorschrift
A suspension of 2-amino-6-methoxy-N-methylbenzamide (8.84 g, 49.07 mmol), N-(1,3-dimethyl-1H-pyrazol-5-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (12.5 g, 32.71 mmol), diacetoxypalladium (0.367 g, 1.64 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (1.893 g, 3.27 mmol) and cesium carbonate (19.18 g, 58.88 mmol) in dioxane (130 mL) was degassed with argon, which was also let to bubble for 10 minutes then stirred at reflux for 6h. The reaction mixture was allowed to cool to rt, the insolubles were removed by filtration, washed with EtOAc and the filtrate was concentrated. (Insolubles~23g). The crude product (20g) was purified by flash chromatography on silica gel eluting with 0 to 5% methanol in ethyl acetate. The solvent was evaporated to dryness to afford a foam (7.9g) which was taken up into dichloromethane (40ml) (no time to get dissolved, it crashed out very quickly) and sonicated for 5 minutes. The resulting precipitate was collected by filtration, washed with dichloromethane and dried under vacuum at 50°C to a constant weight to afford 2-(2-(1,3-dimethyl-1H-pyrazol-5-ylamino)-5-(trifluoromethyl)pyridin-4-ylamino)-6-methoxy- N-methylbenzamide (6.53 g, 46.0 %) as a white solid. The filtrate was concentrated to dryness (residue weight: 700mg), taken up into DCM and collected by filtration to give a second sample EN02972-51-02 (0.36 g, 0.829 mmol, 2.53 %).