Methyl 3-bromopropanoate → HCID 21699804, compound

Participants

Reaction Steps

To a stirred solution of naphthyridine 23-1 (Hamada, Y. et al., Chem. Pharm. Bull. Soc., 1971, 19(9), 1857-1862), (2.2 g, 15.2 mmol) and THF (200 ml) at -78° C. was added NaN(TMS)2 (1M/THF, 18 ml, 18 mmol) dropwise over a 20 min period. After 30 minutes at -78° C., methyl 3-bromopropionate was added in a stream. After 30 min, the reaction was quenched with 50 ml 10% KHSO4. The mixture was extracted with Et2O. The remaining aqueous portion was basified with sat. NaHCO3 and then extracted with EtOAc. The EtOAc portion was washed with brine, dried (MgSO4) and concentrated. Flash chromatography (silica, 2% EtOH/EtOAc) gave the ester 23-2 (1.61 g) as a yellow oil.

Provenance & Evidence