Ethyl Acetate → HCID 70663192, compound

HRID 878250Notes

Reaction equation

HRID 878250 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]([CH3:32])[C:15](=[O:31])[C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18](SCCOC)[CH:17]=2)=[C:4]([O:33][CH3:34])[CH:3]=1.O[O:36][S:37]([O-:39])=O.[K+].[NH4+].[Cl-].[CH3:43][CH2:44][O:45][C:46](C)=O>CO.O>[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]([CH3:32])[C:15](=[O:31])[C:16]2[CH:21]=[C:20]([C:22]([F:23])([F:25])[F:24])[CH:19]=[C:18]([S:37]([CH2:43][CH2:44][O:45][CH3:46])(=[O:39])=[O:36])[CH:17]=2)=[C:4]([O:33][CH3:34])[CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 23707502Potassium hydroxy sulfiteHCID 70663490HCID 70663490, compound

Product 1

HCID 70663192HCID 70663192, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To an ice-cold solution of N-(4-(4-fluoro-2-methoxyphenyl)pyridin-3-yl)-3-(2-methoxyethylthio)-N-methyl-5-(trifluoromethyl)benzamide (0.032 g, 64.7 μmol) in MeOH (4 mL) and water (0.5 mL) was added Oxone® (99.5 mg, 162 μmol) and the reaction mixture was stirred at room temperature for 4.5 hours. The white suspension was poured on saturated aqueous NH4Cl solution and EtOAc. The two layers were separated. The aqueous layer was extracted twice with EtOAc. The organic layers were washed once with aqueous sodium thiosulfate 10% solution and once with brine, dried over MgSO4, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 5 g column using an MPLC (ISCO) system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Colorless solid (0.027 g; 79%). MS (ESI): m/z=527.13 [M+H]+.

Workup

  1. customThe two layers were separated
  2. extractionThe aqueous layer was extracted twice with EtOAc
  3. washThe organic layers were washed once with aqueous sodium thiosulfate 10% solution and once 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 5 g column
  9. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)

Sources & evidence

ORD record
ord-445697046d474b1793d7113acccf9110
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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