Cesium carbonate → HCID 89761884, Verbindung

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

In a reaction vial flushed with nitrogen, 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (1.080 ml, 6.38 mmol), 4-(2-bromo-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (EXAMPLE 53, Step 1; 1.022 g, 1.596 mmol), PdCl2(dppf)-CH2Cl2 adduct (0.065 g, 0.080 mmol), and cesium carbonate (1.560 g, 4.79 mmol) were combined in dioxane (7.18 ml) and water (0.798 ml). The vial was sealed and heated at 100° C. overnight. The reaction was diluted with ethyl acetate and extracted with water. The aqueous layer was then back extracted with ethyl acetate (×3). The organics were combined and dried over sodium sulfate, filtered and concentrated to yield crude material, which was then purified via silica gel chromatography (eluting with 0-100% ethyl acetate in heptanes) to yield N-(4-methoxybenzyl)-N-(thiazol-2-yl)-4-(4-(trifluoromethyl)-2-vinylphenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (0.787 g, 1.339 mmol, 84% yield) as a light yellow solid. m/z (ESI) 588.3 (M+H)+.

Herkunft & Nachweise