With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.25637-16-5,4-Bromotetrahydropyran,as a common compound, the synthetic route is as follows.,25637-16-5
4-Bromooxane (3.17 g, 19.2 mmol) was added drop wise to a stirred suspension of magnesium (466 mg, 19.2 mmol) and one crystal of iodine in THF (26 mL) at ambient temperature. The reaction mixture was stirred for 30 min before it was cooled to 0C. 3- Fluoropicolinaldehyde (1.20 g, 9.59 mmol) was added drop wise. The reaction mixture was then stirred for 30 min. The reaction mixture was quenched with saturated aqueous ammonium chloride (40 mL) and diluted with ethyl acetate (100 mL) and water (30 mL). The product was extracted into the organic phase before the layers were separated. The aqueous layer was washed with a second portion of ethyl acetate (50 mL), and the combined organics were dried over sodium sulfate. The volatiles were removed under reduced pressure. The crude reaction material was purified using silica gel column chromatography. (3-Fluoropyridin-2-yl)(oxan-4-yl)methanol (1.47 g, 6.96 mmol, 73 % yield) was isolated as a colorless oil. NMR (400 MHz, CDCh) delta 8.40-8.45 (m, 1H), 7.40-7.46 (m, 1H), 7.27-7.33 (m, 1H), 4.83-4.88 (m, 1H), 4.00 (td, J=2.14, 11.37 Hz, 2H), 3.36 (ddt, J=2.20, 9.23, 11.77 Hz, 2H), 1.90-2.03 (m, 1H), 1.65-1.78 (m, 1H), 1.57 (dq, J=4.65, 12.47 Hz, 1H), 1.39-1.49 (m, 2H).
The synthetic route of 25637-16-5 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; VACCARO, Wayne; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; DELUCCA, George V.; DESKUS, Jeffrey A.; HAN, Wen-Ching; KUMI, Godwin Kwame; SCHMITZ, William D.; STARRETT, John E., JR.; HILL, Matthew D.; HUANG, Hong; (563 pag.)WO2016/183118; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics