Tetrabutylammonium Fluoride → HCID 18675453, compound

HRID 1635037Notes

Reaction equation

HRID 1635037 reaction equation
CS([N:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14](=[O:22])[C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)=[CH:11][CH:12]=2)[C:7]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)=[CH:6]1)(=O)=O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:29][C:25]1[CH:24]=[C:23]([C:7]2[C:8]3[C:13](=[CH:12][CH:11]=[C:10]([C:14](=[O:22])[C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=4)[CH:9]=3)[NH:5][CH:6]=2)[CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 12020314HCID 12020314, compound

Product 1

HCID 18675453HCID 18675453, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-methylsulfonyl-3-(3-chlorophenyl)-5-(4-chlorobenzoyl)indole (11.44 g, 25.76 mmol, see Preparation 7) in anhydrous THF (150 ml) was added tetrabutylammonium fluoride (33.5 ml, 1.0 M solution in THF). The resulting solution was refluxed under nitrogen for about 3 hrs. The solvent was removed under reduced pressure. The residue was dissolved in EtOAc and washed with 1N HCl (2 times), saturated NaHCO3 aqueous solution (2 times) and brine (2 times), dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica, eluting with EtOAc/hexane 1:4. The title compound was obtained as a yellow solid. Yield=8.1 g, 86%.

Workup

  1. temperatureThe resulting solution was refluxed under nitrogen for about 3 hrs
  2. customThe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with 1N HCl (2 times), saturated NaHCO3 aqueous solution (2 times) and brine (2 times)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography on silica
  9. washeluting with EtOAc/hexane 1:4

Sources & evidence

ORD record
ord-8b75e82a21204205800e2a9ec1c1cdae
Source dataset
uspto-grants-2003_01
Patent number
US06509336B1

Reaction notes

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