Hydrochloric Acid → HCID 45279721, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(4-chlorobenzyl)-4-oxo-4H-quinolizine-3-carboxylic acid (0.060 g, 0.19 mmol) in 2 mL of THF under N2(g) was added phenylboronic acid (0.035 g, 0.29 mmol), 1 N cesium carbonate (0.38 mL, 0.38 mmol), and bis (tri-tert-butylphosphine) palladium(0). The reaction was heated to 100° C. for 15 h, cooled to rt, and acidified with 6 N HCl to pH ˜3. The mixture was then filtered and subjected to purification via reverse phase HPLC to yield the title compound that gave a mass ion (ES+) of 356.0 for M+H+. 1H NMR (400 MHz, d6-DMSO) δ 9.40 (d, J=7.2 Hz, 1H), 8.41 (s, 1H), 8.23 (d, J=9.0 Hz, 1H), 8.09-8.05 (m, 1H), 7.69 (d, J=6.9 Hz, 1H), 7.63-7.58 (m, 4H), 7.46-7.42 (m, 2H), 7.35-7.33 (m, 3H), 4.39 (s, 2H).

Provenance & Evidence