Electric Literature of 156094-63-2 , The common heterocyclic compound, 156094-63-2, name is 2-(Bromomethyl)-6-methoxypyridine, molecular formula is C7H8BrNO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
General procedure: To a flame-dried flask containing z-BuOK (1.10 equiv.) and anhydrous DMF (2.5 mL/mmol) was added ethyl 2-((diphenylmethylene)amino)acetate (1.05 eq. ) at 0 C under argon. After 10 min, arylmethyl bromide (1.0 eq.) was added. The resulting reaction mixture was stirred at 0 C for 10 min and was allowed to warm up to 4 C and stirred at 4 C overnight. The reaction mixture was then slowly poured into water, extracted with DCM. The combined organic layers were dried over Na SCfl, filtered and concentrated under reduced pressure to evaporate the DCM solvent. The residue was then treated with a mixture of EtOH/concentrated HC1 (25:1 v/v). The resulting solution was stirred at room temperature for 2 h. Upon the evaporation of EtOH and most of the DMF, the residue was basified by 2 N K2CO3 solution to pH > 10 and extracted with DCM. The combined organic layers were dried over Na SCfl, filtered and concentrated under reduced pressure. The residue was purified through flash chromatography on silica gel (1: 19 CH3OH/CH2CI2) to afford the desired ethyl 2-amino-3- arylpropanoate product as a colorless gel.
The synthetic route of 156094-63-2 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; DE BRABANDER, Jef; ROSENBAUM, Daniel; LIANG, Qiren; WANG, Wentian; (343 pag.)WO2019/191327; (2019); A1;,
Pyridine – Wikipedia,
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