Electric Literature of 130722-95-1, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 130722-95-1, name is 3-(Benzyloxy)-5-bromopyridine. A new synthetic method of this compound is introduced below.
To a stirred solution of 3-(benzyloxy)-5-bromopyridine (1 g, 3.7 mmol) in toluene (25 mL), were added tris(dibenzylideneacetone)dipalladium(0) (169 mg, 0.185 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (230 mg, 0.37 mmol) and sodium tert-butoxide (710 mg, 7.4) and the flask was purged with argon. Thiomorpholine 1,1-dioxide (766 mg, 5.68) was added to the mixture and heated to 80 oC for 14 hours. After the completion of the reaction (monitored by TLC) the solvent was removed under vacuum. Water was added (10 mL) and the mixture was extracted with ethyl acetate (3×30 mL). The combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified on silica gel (Biotage; eluting solvents DCM: MeOH 10/1 ratio) to obtain red oil (720 mg, 60% yield); 1H NMR (500 MHz, CDCl3) delta 7.96 (m, 2H), 7.41-7.34 (m, 5H), 6.75 (t, J = 2.2 Hz, 1H), 5.10 (s, 2H), 3.85 – 3.83 (m, 4H), 3.08 – 3.06 (m, 4H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound,130722-95-1, 3-(Benzyloxy)-5-bromopyridine, and friends who are interested can also refer to it.
Reference:
Article; Lamani, Manjunath; Malamas, Michael S.; Farah, Shrouq I.; Shukla, Vidyanand G.; Almeida, Michael F.; Weerts, Catherine M.; Anderson, Joseph; Wood, JodiAnne T.; Farizatto, Karen L.G.; Bahr, Ben A.; Makriyannis, Alexandros; Bioorganic and Medicinal Chemistry; vol. 27; 23; (2019);,
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