Cesium carbonate → HCID 53318822, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 1-[(6-bromo-3,4-dihydroisoquinolin-2(1H)-yl)methyl]-4-oxo-4H-quinolizine-3-carboxylate (0.045 g, 0.10 mmol), phenylboronic acid (0.019 g, 0.15 mmol), and 1 N cesium carbonate (0.20 mL, 0.20 mmol) in 1 mL THF under nitrogen was added bis (tri-tert-butyl-phosphine)palladium(0) (10 mol %). The reaction mixture was stirred at 100° C. for 3 hours, then cooled to rt and concentrated in vacuo. To a solution of the resultant brown residue in 1 mL DMSO was added saturated aqueous lithium hydroxide (0.3 mL). After 2 hours, the reaction was filtered and subjected to purification via reverse phase HPLC to provide the title compound which gave a mass ion (ES+) of 411.0. 1H NMR (400 MHz, DMSO) δ 10.2 (br s, 1H), 9.46 (d, J=6.2 Hz, 1H), 8.74 (s, 1H), 8.60-8.56 (m, 1H), 8.32-8.08 (m, 2H), 7.78-7.75 (m, 1H), 7.67-7.65 (m, 2H), 7.57-7.55 (m, 1H), 7.48-7.44 (m, 2H), 7.38 (d, J=7.4 Hz, 1H), 7.32-7.12 (m, 1H), 4.94 (s, 2H), 4.64-4.50 (m, 2H), 3.82-3.38 (m, 2H), 3.18-3.07 (m, 2H).

Provenance & Evidence