Citric Acid → N-[4-(4-Fluoro-2-methoxy-phenyl)-pyridin-3-yl]-3-mercapto-5,N-dimethyl-benzamide

HRID 878247Notes

Reaction equation

HRID 878247 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N:14]([CH3:34])[C:15](=[O:33])[C:16]2[CH:21]=[C:20]([S:22]CC[Si](C)(C)C)[CH:19]=[C:18]([C:29](F)(F)F)[CH:17]=2)=[C:4]([O:35][CH3:36])[CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.CCOC(C)=O>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N:14]([CH3:34])[C:15](=[O:33])[C:16]2[CH:17]=[C:18]([CH3:29])[CH:19]=[C:20]([SH:22])[CH:21]=2)=[C:4]([O:35][CH3:36])[CH:3]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 70663298N-(4-(4-fluoro-2-methoxyphenyl)pyridin-3-yl)-N-methyl-3-(trifluoromethyl)-5-(2-(trimethylsilyl)ethylthio)benzamide

Product 1

HCID 70663151N-[4-(4-Fluoro-2-methoxy-phenyl)-pyridin-3-yl]-3-mercapto-5,N-dimethyl-benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(4-(4-fluoro-2-methoxyphenyl)pyridin-3-yl)-N-methyl-3-(trifluoromethyl)-5-(2-(trimethylsilyl)ethylthio)benzamide (0.711 g, 1.32 mmol) in THF (12.6 mL) was added tetrabutylammonium fluoride (1M solution in THF, 6.96 mL, 6.96 mmol) and the clear light yellow solution was stirred at room temperature for 90 minutes. The reaction mixture was poured on 10% aqueous citric acid solution and EtOAc and the layers were separated. The aqueous layer was extracted twice with EtOAc. The organic layers were washed with brine, dried over MgSO4, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 20 g column using an MPLC system eluting with a gradient of CH2Cl2:MeOH (100:0 to 90:10). Colorless solid (0.41 g; 63%). MS (ESI): m/z=437.09 [M+H]+.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted twice with EtOAc
  3. washThe organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. additiontreated with silica gel
  7. customevaporated
  8. customThe compound was purified by silica gel chromatography on a 20 g column
  9. washeluting with a gradient of CH2Cl2:MeOH (100:0 to 90:10)

Sources & evidence

ORD record
ord-f9d50de582144eafbf53be089355d113
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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