Hydrochloric Acid → HCID 56644527, compound

HRID 508404

Reaction equation

HRID 508404 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].Br[CH2:14][C:15]1[C:27]([F:28])=[CH:26][C:18]([C:19]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[O:20])=[C:17]([F:29])[CH:16]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[C:8]([F:10])([F:11])[F:9])[O:12][CH2:14][C:15]1[C:27]([F:28])=[CH:26][C:18]([C:19]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[O:20])=[C:17]([F:29])[CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 136091473-Chloro-4-(trifluoromethyl)phenolHCID 666671114-(Bromomethyl)-2,5-difluoro-N-(methylsulfonyl)benzamide

Product 1

HCID 56644527HCID 56644527, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 3-chloro-4-(trifluoromethyl)phenol (Preparation 5, 50 mg, 0.26 mmol), 4-(bromomethyl)-2,5-difluoro-N-(methylsulfonyl)benzamide (Preparation 4, 84 mg, 0.26 mmol) and potassium carbonate (71 mg, 0.51 mmol) in dimethyl sulfoxide (5 mL) was stirred at room temperature for 16 hours. A 2M aqueous solution of hydrogen chloride was added to the reaction mixture. The resulting precipitate was filtered, washed with diethyl ether (5 mL) and dried. The material was purified by reverse phase column chromatography (12 g C-18 biotage cartridge; eluents: MeCN+0.1% formic acid, and H2O+0.1% formic acid; Gradient: 30% MeCN, followed by gradient to 100% MeCN, 100% MeCN. Fractions containing product were combined and concentrated in vacuo to afford the title compound as a colourless solid (65 mg, 56%).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with diethyl ether (5 mL)
  3. customdried
  4. customThe material was purified by reverse phase column chromatography (12 g C-18 biotage cartridge
  5. additionFractions containing product
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0d6188b512ea48448d6dfeff5f43094f
Source dataset
uspto-grants-2015_08
Patent number
US09096500B2

Linked notes

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