Water → HCID 117653514, compound

HRID 2178116Notes

Reaction equation

HRID 2178116 reaction equation
[Br:1][C:2]1[C:3](F)=[CH:4][C:5]([F:30])=[C:6]([S:8]([N:11]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=2[O:28][CH3:29])[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][N:13]=2)(=[O:10])=[O:9])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].[F:38][C:39]1[CH:46]=[C:45]([OH:47])[CH:44]=[CH:43][C:40]=1[C:41]#[N:42].O>CS(C)=O.[Cl-].[Na+].O>[Br:1][C:2]1[C:3]([O:47][C:45]2[CH:44]=[CH:43][C:40]([C:41]#[N:42])=[C:39]([F:38])[CH:46]=2)=[CH:4][C:5]([F:30])=[C:6]([S:8]([N:11]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=2[O:28][CH3:29])[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][N:13]=2)(=[O:9])=[O:10])[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27346752-Fluoro-4-hydroxybenzonitrileHCID 117653159HCID 117653159, compound

Product 1

HCID 117653514HCID 117653514, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 5-bromo-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(5-fluoropyridin-2-yl)benzenesulfonamide (Preparation 12, 425 mg, 0.90 mmol) in DMSO (5 mL) was added K2CO3 (372 g, 2.70 mmol) followed by 2-fluoro-4-hydroxybenzonitrile (123 g, 0.90 mmol). The reaction mixture was left to stir at room temperature for 18 hours. To the reaction mixture was added water (20 mL) and saturated brine (20 mL) and the product was extracted with EtOAc (50 mL). The organic layer was retained and washed with saturated brine (3×40 mL), dried over MgSO4, and the solvent removed under vacuum. The residue was purified using silica gel column chromatography eluting with 15% EtOAc in heptanes followed by trituration with heptane to afford the title compound as a colourless solid (74 mg, 28%).

Workup

  1. waitThe reaction mixture was left
  2. extractionthe product was extracted with EtOAc (50 mL)
  3. washwashed with saturated brine (3×40 mL)
  4. dry with materialdried over MgSO4
  5. customthe solvent removed under vacuum
  6. customThe residue was purified
  7. washeluting with 15% EtOAc in heptanes

Sources & evidence

ORD record
ord-cfdbc210ddef4662bea633406f5c0bd0
Source dataset
uspto-grants-2015_06
Patent number
US09067922B2

Reaction notes

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