Uses
2-Acetamido-6-bromopyridine is a chemical reagent used in the synthesis of diarylureas used as allosteric modulators. Also used in the prouction of novel Bcl-Abl inhibitors with flexible linkers.
Synthesis
I. General procedure for the synthesis of N-(6-bromopyridin-2-yl)acetamide:
Step a: To a solution of 6-bromopyridin-2-amine (10 g, 0.060 mol) and triethylamine (Et3N, 25 g, 0.27 mol) in dichloromethane (CH2Cl2, 300 mL) was slowly added acetyl chloride (AcCl, 13 g, 0.17 mol) at 0°C. The reaction mixture was stirred overnight at room temperature. After completion of the reaction, the reaction mixture was diluted with water and extracted with ethyl acetate (EtOAc, 200 mL x 3). The organic layers were combined, dried over anhydrous sodium sulfate (Na2SO4) and subsequently concentrated under reduced pressure to afford N-(6-bromopyridin-2-yl)acetamide (88% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 8.15 (d, J = 8.0 Hz, 1H), 7.97 (brs, 1H), 7.55 (t, J = 8.0 Hz, 1H), 7.18 (d, J = 8.0 Hz, 1H), 2.19 (s, 3H).
References
[1] Patent: WO2012/119979, 2012, A1. Location in patent: Page/Page column 34-35
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 15, p. 4730 - 4743
[3] Patent: WO2008/141119, 2008, A2. Location in patent: Page/Page column 84
[4] Patent: US2004/92741, 2004, A1. Location in patent: Page 4
[5] Patent: US2009/176842, 2009, A1. Location in patent: Page/Page column 13
