Tert-Butanesulfinamide → HCID 11326499, compound

HRID 457271Notes

Reaction equation

HRID 457271 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3](=O)[CH2:4][C:5]([C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[O:15][CH3:16])([CH3:7])[CH3:6].[C:20]([S:24]([NH2:26])=[O:25])([CH3:23])([CH3:22])[CH3:21]>CCO.C1COCC1.[Cl-].[Na+].O.CCOC(C)=O>[F:14][C:12]1[CH:11]=[CH:10][C:9]([O:15][CH3:16])=[C:8]([C:5]([CH3:7])([CH3:6])[CH2:4]/[C:3](=[N:26]/[S:24]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:25])/[C:2]([F:19])([F:18])[F:1])[CH:13]=1

Participants

7

Reactant 2

HCID 3382465Tert-ButanesulfinamideHCID 100849201,1,1-Trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-one

Product 1

HCID 11326499HCID 11326499, compoundYield 44%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a mixture of 500 mg (1.8 mmol) of 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-one (Example 1) and 0.86 mL (3.6 mmol) of a solution of Ti(OEt)4 in EtOH (˜20% Ti) in 7 mL of THF was added 240 mg (2 mmol) t-butylsulfinamide. The reaction was warmed at reflux for 6 h and then cooled to room temperature, diluted with 1 mL of brine and EtOAc, filtered through diatomaceous earth and concentrated to afford an oil. The residue was absorbed onto silica gel and chromatographed on silica gel eluting with hexanes-EtOAc (98:2) to afford 300 mg (44%) of 2-methylpropane-2-sulfinic acid [3-(5-fluoro-2-methoxyphenyl)-3-methyl-1-trifluoromethylbut-(Z)-ylidene]-amide as an orange oil.

Workup

  1. temperatureThe reaction was warmed
  2. temperatureat reflux for 6 h
  3. filtrationfiltered through diatomaceous earth
  4. concentrationconcentrated
  5. customto afford an oil
  6. customThe residue was absorbed onto silica gel
  7. customchromatographed on silica gel eluting with hexanes-EtOAc (98:2)

Sources & evidence

ORD record
ord-b531b39fec9d4d7fb2a7c99b0551e3c7
Source dataset
uspto-grants-2007_03
Patent number
US07186864B2

Reaction notes

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