N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamide

Synthesis

General procedure for the synthesis of 2-acetamido benzothiazole-6-boronic acid from 6-bromo-2-acetamidobenzothiazole and pinacol ester of bis(pinacolato): N-(6-bromobenzo[d]thiazol-2-yl)acetamide (2.10 g, 7.75 mmol), bis(pinacolato)diboron (3.00 g, 11.8 mmol), Pd(dppf)Cl2 ( 560 mg, 0.77 mmol) and KOAc (3.00 g, 30.6 mmol) were dissolved in DMSO (50 mL) and the reaction was stirred at 90 °C for 8 h under N2 atmosphere. After completion of the reaction, it was cooled to room temperature and the reaction mixture was filtered. The filtrate was diluted with ethyl acetate (200 mL), washed sequentially with brine (20 mL x 3) and the organic phase was dried over anhydrous Na2SO4 and concentrated. The resulting residue was washed with petroleum ether (50 mL) to give the light brown solid product 2-acetamido benzothiazole-6-boronic acid (2.40 g, 97% yield).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 17, p. 3665 - 3670
[2] Patent: WO2018/17435, 2018, A1. Location in patent: Paragraph 0092-0093
[3] Patent: CN107753483, 2018, A. Location in patent: Paragraph 0036; 0038; 0041-0042
[4] Patent: US2015/225407, 2015, A1. Location in patent: Paragraph 0410
[5] Patent: WO2010/100144, 2010, A1. Location in patent: Page/Page column 101-102