Sodium Iodide → HCID 56597937, compound

Participants

Reaction Steps

A mixture of intermediate 3 (142 mg, 0.5 mmol) and NaI (150 mg, 1.0 mmol) in CH3CN was heated to reflux for 30 min and then cooled to rt. Intermediate 2 (196 mg, 0.7 mmol) and anhydrous K2CO3 (173 mg, 1.25 mmol) were added to the mixture. The resulting mixture was heated to reflux for 4 h. Precipitated crystals were filtered off and the filtrate was evaporated under reduced pressure. The residue was extracted with EtOAc. The combined EtOAc layers were washed with brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by flash chromatography on silica gel column (elution with DCM/MeOH=30:1) to give 7-(3-(4-(2,3-dichlorophenyl)-1,4-diazepan-1-yl)propoxy)-3,4-dihydroquinolin-2(1H)-one (compound 1) (140 mg, 63%). 1H NMR (300 MHz, CDCl3): δ 8.16 (s, 1H), 7.10-6.98 (m, 4H), 6.53 (dd, J=8.1 Hz, 2.4 Hz, 1H), 6.34 (d, J=2.1 Hz, 1H), 4.01 (t, J=6.6 Hz, 2H), 3.32-3.28 (m, 4H), 2.92-2.87 (m, 6H), 2.76 (t, J=6.6 Hz, 2H), 2.62 (t, J=6.6 Hz, 2H), 2.04-1.97 (m, 4H). HPLC: 99%, RT 2.421 min. MS (ESI) m/z 448.1 [M+H]+. mp: 130-131° C.

Provenance & Evidence