Sodium Iodide → HCID 18332408, compound

Participants

Reaction Steps

1-(2-Chloroethyl)-3,4-dihydro-3,3-dimethyl-6-methylsulfonyl-2(1H)-quinolinone (1.0 g, 0.0032 mol), 6-fluoro-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (0.684 g, 0.0032 mol), sodium iodide (0.15 g, 0.001 mol) and potassium carbonate (1.38 g, 0.010 mol) were suspended in acetonitrile (45 ml). The reaction mixture was heated at reflux under nitrogen for 20 hr. The product mixture was then cooled to room temperature. The solvent was evaporated in vacuo. The residue was dissolved in ethyl acetate (50 ml) and washed with water (50 ml). The organic layer was then dried (MgSO4), filtered and concentrated in vacuo. The residue was chromatographed to afford 1-[2-[4-(6-fluoro-1H-indol-3-yl)-3,6-dihydro-1(2H)-pyridinyl]ethyl]-3,4-dihydro-3,3-dimethyl-6-methylsulfonyl-2(1H)-quinolinone as a yellow foam. δ(1H NMR, DMSO, ppm): 1.28 (6H, s), 2.68 (2H, m), 3.14 (2H, s), 3.40 (3H, s), 3.55 (3H, br), 3.96 (1H, br), 4.06 (1H, br), 4.30 (1H, d), 4.60 (2H, t), 6.36 (1H, s), 7.11 (1H, dt), 7.35 (1H, dd), 7.78 (2H, m), 8.00 (3H, m), 11.56 (1H, s).

Provenance & Evidence