Nitrogen → Ethyl 3-(5-bromopyridin-2-yl)propanoate

Participants

Reaction Conditions

Reaction Steps

A solution of Zn metal (18 g, 0.27 mol) in DMF (5 mL) was purged with N2. BrCH2CH2Br (2.0 g, 10 mmol) was added, followed by TMSCl (0.92 g, 8.5 mmol). The resulting mixture was stirred at 90° C. for 30 min, and allowed to cool to rt. A solution of compound 57a (50 g, 0.22 mol) in DMF (150 mL) was added, and the resulting mixture was stirred overnight at rt. Pd(PPh3)2Cl2 (7.4 g, 10 mmol) was added, followed by 2,5-dibromopyridine (50 g, 0.21 mol). The resulting mixture was stirred at 68° C. for 2 h. The reaction was quenched by the addition of saturated NaHCO3 solution (300 mL). The resulting solution was extracted with EtOAc (2×100 mL), and the combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue obtained was purified by flash column chromatography on silica gel (EtOAc/petroleum ether (1:2 v/v)) to obtain compound 57b as a yellow oil. Mass Spectrum (LCMS, ESI pos.): Calcd. for C10H12BrNO2: 258.0 (M+H). Found: 258.2.

Provenance & Evidence