Ammonium Chloride → HCID 58360364, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,5-dibromopyridine (1.00 g, 4.22 mmol) in 50 mL of toluene at −78° C. was added n-BuLi (2.0 mL, 5.0 mol, 2.5 M in THF) dropwise. After 2 h, ethyl 1-formyl-4-oxo-4H-quinolizine-3-carboxylate (1.35 g, 5.5 mmol) was added. The reaction was stirred at −78° C. for another 1 h, then transferred to a 0° C. ice water bath. After an additional 1 h at 0° C., saturated aqueous ammonium chloride (10 mL) was added. The mixture was warmed to rt and filtered to remove an insoluble brown solid. The filtrate was separated, and the organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The resultant residue was subjected to purification via silica gel chromatography from 0-5% MeOH in CH2Cl2 to yield crude ethyl 1-[(5-bromopyridin-2-yl)(hydroxy)methyl]-4-oxo-4H-quinolizine-3-carboxylate that gave a mass ion (ES+) of 402.9 (79Br) for M+H+.

Provenance & Evidence