[C:1]([NH:4][C:5]([NH:7][C:8]1[C:13]([F:14])=[CH:12][C:11]([Br:15])=[CH:10][C:9]=1F)=[S:6])(=[O:3])[CH3:2].[H-].[Na+].O>CN(C=O)C>[Br:15][C:11]1[CH:12]=[C:13]([F:14])[C:8]2[N:7]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[S:6][C:9]=2[CH:10]=11-acetyl-3-(4-bromo-2,6-difluorophenyl)thiourea (3.356 g, 10.86 mmol) was dissolved in DMF (100 ml) and the flask was cooled under nitrogen in an ice water bath. Then, sodium hydride (60% in mineral oil, 512.6 mg, 12.82 mmol) was added, and the reaction was warmed to room temperature and stirred for 1 hour. Then, the reaction flask was put in a preheated oil bath (130° C.) and stirred under nitrogen for an additional hour. The reaction was cooled to room temperature, poured into deionized water (300 ml), and filtered. The solid was washed with water and then dried by suction overnight to afford N-(6-bromo-4-fluorobenzo[d]thiazol-2-yl)acetamide (3.205 g, ˜100%). MS (ESI pos. ion) m/z: 289 (MH+, 79Br), 291 (MH+, 81Br). Calculated exact mass for C9H6BrFN2OS 288 (79Br), 290 (81Br).
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