HCID 58157157, compound → HCID 53322866, 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) in 1 mL THF under nitrogen was added 1.0 M dimethylzinc solution in THF (0.112 mL, 0.112 mmol), and tetrakis(triphenylphosphine)palladium (0) (10 mol %). The reaction mixture was stirred at 60° C. for 4 hours, quenched with 1 mL of saturated aqueous ammonium chloride, 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 acidified with 1 N HCl to pH ˜2, filtered and subjected to purification via reverse phase HPLC to provide the title compound which gave a mass ion (ES+) of 349.0. 1H NMR (400 MHz, DMSO) δ 10.07 (br s, 1H), 9.46 (d, J=6.8 Hz, 1H), 8.70 (s, 1H), 8.53 (d, J=8.4 Hz, 1H), 8.22-8.19 (m, 1H), 7.76 (t, J=6.6 Hz, 1H), 7.20-6.97 (m, 3H), 4.89 (s, 2H), 4.40-4.34 (m, 2H), 3.76-3.60 (m, 2H), 3.10-3.02 (m, 2H), 2.26 (s, 3H).

Provenance & Evidence