Ammonium Chloride → 7-(Dimethoxymethyl)-1,2,3,4-tetrahydro-6-methoxy-1,8-naphthyridine

Participants

Reaction Conditions

Reaction Steps

A solution of 6-bromo-7-(dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine (intermediate 2, 253 mg, 0.881 mmol) in MeOH (0.85 ml) under argon was treated with NaOMe (5.4 M in MeOH, 0.816 ml, 4.41 mmol), flushed with argon, treated with CuBr (253 mg, 1.76 mmol). The vial was sealed and the reaction mixture was stirred at 120° C. for 15 h. The reaction mixture was cooled to room temperature, treated with sat. aq. NH4Cl and extracted with EtOAc (2×). The combined org. layers were washed again with brine, dried over Na2SO4 and concentrated. The crude material was purified by normal phase chromatography (12 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100) to give the title compound as a pale yellow oil. (UPLC-MS 1) tR 0.73 min; ESI-MS 239.1 [M+H]+.

Provenance & Evidence