Cesium carbonate → HCID 66559507, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 7-hydroxy-3,4-dihydroquinolin-2(1H)-one (228 mg, 1.4 mmol) in NMP was added Cs2CO3 (456 mg, 1.4 mmol). The slurry was degassed by evacuating and filling the reaction flask with N2 three times. Intermediate 54 (280 mg, 0.7 mmol) and TMHD (13 mg, 0.07 mmol) were added followed by the addition of CuCl (70 mg, 0.7 mmol). The reaction mixture was degassed by evacuating and filling the reaction flask with N2 three times, and then warmed to 120° C. under N2 for 7.5 h. The reaction mixture was cooled to rt and diluted with Et2O. The slurry was filtered and the filtercake was washed with Et2O. Combined filtrates were washed with 2 N HCl, 0.6 N HCl, 2 M NaOH, and 10% aq NaCl. The resulting organic layer was dried, concentrated, and purified by flash chromatography on a silica gel column (elution with PE/EtOAc=1:1) to give 7-(4-((4-(2,3-dichlorophenyl)piperazin-1-yl)methyl)phenoxy)-3,4-dihydro quinolin-2(1H)-one (compound 31) (120 mg, 35%). 1H NMR (300 MHz, CDCl3): δ 7.67 (s, 1H), 7.32 (d, J=8.7 Hz, 2H), 7.16-7.09 (m, 3H), 6.98-6.94 (m, 3H), 6.64-6.61 (m, 1H), 6.41 (d, J=3.0 Hz, 1H), 3.56 (s, 2H), 3.07 (m, 4H), 2.94 (t, J=6.6 Hz, 2H), 2.66-2.61 (m, 6H). HPLC: 99%, RT 2.626 min. MS (ESI) m/z 482.1 [M+H]+. mp: 185-186° C.

Provenance & Evidence