1-Bromo-2-ethylbenzene → 4-(2-ethylphenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

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A mixture of N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (1.0 g, 2.39 mmol), 1-bromo-2-ethylbenzene (572.0 mg, 3.11 mmol, Aldrich), Pd2(dba)3 (218 mg, 0.23 mmol, GLR), Xantphos (276 mg, 0.46 mmol, GLR) and sodium-tert-butoxide (458 mg, 4.784 mmol) in toluene (20 mL) was degassed with nitrogen for 10 minutes. The reaction mixture was heated at 100° C. for 1 h under microwave irradiation. After completion, reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain the crude material which was purified by combiflash column chromatography (column size: 12 g; elution: 0-20% ethyl acetate in hexane) to obtain 4-(2-ethylphenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (400 mg, 33%) as a brown solid. MS (ESI, positive ion) m/z; 522.1 (M+1)

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