Methyl 2-bromobenzoate → HCID 89761814, compound

Participants

Reaction Steps

A mixture of N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (Intermediate M; 500 mg, 1.196 mmol), methyl 2-bromobenzoate (687 mg, 2.99 mmol, Spectrochem), Pd2(dba3)2 (109 mg, 0.119 mmol), Xantphos (138 mg, 0.239 mmol) and sodium-tert-butoxide (229 mg, 2.392 mmol) in toluene (10 mL) was degassed for 10 minutes. The reaction mixture was subjected to microwave for 1 h at 100° C. After completion, reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (3×15 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain the crude material which was purified by combi flash column chromatography (column size: 12 g; elution: 0-20% ethyl acetate in hexane) to get methyl 2-(7-(N-(4-methoxybenzyl)-N-(thiazol-2-yl)sulfamoyl)-2H-benzo[b][1,4]oxazin-4(3H)-yl)benzoate (500 mg, 75.7%) as a yellow solid. MS (ESI, positive ion) m/z; 552.1 (M+1)

Provenance & Evidence