Cesium carbonate → 3-Bromo-5-(1,1-dioxo-1lambda6-[1,2]thiazinan-2-yl)-benzoic acid methyl ester

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Reaction Conditions

Reaction Steps

To a sealable tube equipped with a stir bar were added 3-bromo-5-iodobenzoate (2.0 g, 5.88 mmol), cesium carbonate (2.85 g, 8.82 mmol), tris(dibenzylideneacetone)dipalladium (0) (27.1 mg, 0.029 mmol) and xant phos (51 mg, 0.088 mmol) in toluene (45 mL) followed by [1,2]thiazinane 1,1-dioxide (902 mg, 6.47 mmol). The resulting mixture was stirred at 10° C. for 16 h, cooled to room temperature and diluted with ethyl acetate. The organic phase was washed with saturated sodium bicarbonate solution, dried over magnesium sulfate, filtered and concentrated under vacuum. The crude mixture was purified by reverse phase prep HPLC to give the title compound (1.7 g, 84% yield): 1H NMR (CD3OD, 500 MHz) δ ppm 1.93-1.97 (2H, m), 2.30-2.35 (2H, m), 3.30 (2H, t, J=5 Hz), 3.78 (2H, t, J=5 Hz), 3.94 (3H, s), 7.76 (1H, m), 7.93 (1H, m), 8.06 (1H, m). HPLC retention time: 1.772 min (method A). MS (ESI) (M+H)+ 348.06.

Provenance & Evidence