Methanol → N-((3-Bromo-4-fluorophenyl)(2-cyano-3-fluorophenyl)methylene)-2-methylpropane-2-sulfinamide

HRID 1662176Notes

Reaction equation

HRID 1662176 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[F:19])[C:5]([C:7]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[C:8]=1[C:9]#[N:10])=O.[CH3:20][C:21]([S:24]([NH2:26])=[O:25])([CH3:23])[CH3:22].CO.C(=O)(O)[O-].[Na+]>C1COCC1.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[Br:1][C:2]1[CH:3]=[C:4]([C:5]([C:7]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[C:8]=2[C:9]#[N:10])=[N:26][S:24]([C:21]([CH3:23])([CH3:22])[CH3:20])=[O:25])[CH:16]=[CH:17][C:18]=1[F:19]

Participants

7

Reactant 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 3382465Tert-ButanesulfinamideHCID 585794832-(3-Bromo-4-fluoro-benzoyl)-6-fluoro-benzonitrile

Product 1

HCID 76821603N-((3-Bromo-4-fluorophenyl)(2-cyano-3-fluorophenyl)methylene)-2-methylpropane-2-sulfinamideYield 55%

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

2-(3-Bromo-4-fluoro-benzoyl)-6-fluoro-benzonitrile (7.9 g, 24.5 mmol) dissolved in dry THF (40 mL) was added to a solution of titanium (IV) ethoxide (12.7 ml, 61.3 mmol) in dry THF (30 mL) at room temperature. 2-Methyl-2-propanesulfinamide (3.57 g, 29.4 mmol) was added and the resulting mixture was heated at reflux temperature for 22 h. The reaction mixture was cooled to room temperature and methanol (120 mL) was added, followed by addition of saturated sodium bicarbonate (12 mL). The resulting suspension was filtered through a pad of sodium sulfate and the solids were washed thoroughly with ethyl acetate. The filtrate was concentrated in vacuo and purified by flash column chromatography using a gradient of 30-50% ethyl acetate in hexanes to afford 5.7 g (55% yield) of the title compound.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux temperature for 22 h
  3. filtrationThe resulting suspension was filtered through a pad of sodium sulfate
  4. washthe solids were washed thoroughly with ethyl acetate
  5. concentrationThe filtrate was concentrated in vacuo
  6. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-b48e773ef98e438fa28a94f8d8d8d14d
Source dataset
uspto-grants-2011_10
Patent number
US08030500B2

Reaction notes

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