Sodium Iodide → HCID 18332408, compound

HRID 2268785Notes

Reaction equation

HRID 2268785 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[CH:9][C:10]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:11][CH:12]=2)[CH2:7][C:6]([CH3:19])([CH3:18])[C:5]1=[O:20].[F:21][C:22]1[CH:30]=[C:29]2[C:25]([C:26]([C:31]3[CH2:32][CH2:33][NH:34][CH2:35][CH:36]=3)=[CH:27][NH:28]2)=[CH:24][CH:23]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:21][C:22]1[CH:30]=[C:29]2[C:25]([C:26]([C:31]3[CH2:32][CH2:33][N:34]([CH2:2][CH2:3][N:4]4[C:13]5[C:8](=[CH:9][C:10]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:11][CH:12]=5)[CH2:7][C:6]([CH3:19])([CH3:18])[C:5]4=[O:20])[CH2:35][CH:36]=3)=[CH:27][NH:28]2)=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 110530726-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 22595721HCID 22595721, compound

Product 1

HCID 18332408HCID 18332408, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under nitrogen for 20 hr
  3. customThe solvent was evaporated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (50 ml)
  5. washwashed with water (50 ml)
  6. dry with materialThe organic layer was then dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed

Sources & evidence

ORD record
ord-83d6ca21d46e4751a084e6eca92ad6bd
Source dataset
uspto-grants-2001_12
Patent number
US06329366B1

Reaction notes

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