Extracurricular laboratory: Synthetic route of 917023-06-4

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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 917023-06-4, name is Methyl 2-(5-bromopyridin-2-yl)acetate. This compound has unique chemical properties. The synthetic route is as follows. name: Methyl 2-(5-bromopyridin-2-yl)acetate

To a solution of methyl 2-(5-bromopyridin-2-yl)acetate (5.50 g, 23.91 mmol) and 1,4- dioxaspiro[4.5]decan-8-ylmethyl trifluoromethanesulfonate (6.85 g, 19.13 mmol) in THF (100 mL) was added LiHMDS (27.50 mL, 27.50 mmol, 1 M in THF) at -78C. The reaction mixture was stirred at 15C for 16 h under a nitrogen atmosphere. LC-MS showed the reaction was complete. The mixture was quenched with saturated NH4Cl solution (30 mL), diluted with water (60 mL), and extracted with EtOAc (50 mL x 3). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography (SiO2, 0-20% EtOAc/PE) to give the title compound.1H NMR (CDCl3, 400 MHz^^^^^^^^^^G^^J=2.0 Hz, 1H), 7.76 (dd, J=8.4, 2.2 Hz, 1H), 7.20 (d, J=8.6 Hz, 1H), 3.85-3.94 (m, 5H), 3.66 (s, 3H), 2.00-2.05 (m, 1H), 1.79-1.87 (m, 1H), 1.61-1.75 (m, 4H), 1.37-1.47 (m, 2H), 1.17-1.29 (m, 3H). MS (ESI) m/z 384.1/386.1 (M+H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 917023-06-4, Methyl 2-(5-bromopyridin-2-yl)acetate.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SHEN, Dong-Ming; KUANG, Rongze; KUMAR, Puneet; DUFFY, Joseph, L.; ZHU, Cheng; ALI, Amjad; YANG, Meng; DEBENHAM, John, S.; (124 pag.)WO2018/39094; (2018); A1;,
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