Potassium Carbonate → 2,5-Difluoro-N-(methylsulfonyl)-4-[(6-nitropyridin-3-yl)oxy]benzamide

HRID 2048014Notes

Reaction equation

HRID 2048014 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:20]=[C:19]([OH:21])[C:18]([F:22])=[CH:17][C:9]=1[C:10]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[O:11].Br[C:24]1[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[N:28][CH:29]=1>CS(C)=O>[F:7][C:8]1[CH:20]=[C:19]([O:21][C:24]2[CH:29]=[N:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[C:18]([F:22])=[CH:17][C:9]=1[C:10]([NH:12][S:13]([CH3:16])(=[O:14])=[O:15])=[O:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 8176205-Bromo-2-nitropyridineHCID 580424162,5-difluoro-4-hydroxy-N-(methylsulfonyl)benzamide

Product 1

HCID 580424052,5-Difluoro-N-(methylsulfonyl)-4-[(6-nitropyridin-3-yl)oxy]benzamideYield 60.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium carbonate (0.220 g, 1.59 mmol) was added to a stirred solution of 2,5-difluoro-4-hydroxy-N-(methylsulfonyl)benzamide (Preparation 34, 0.200 g, 0.796 mmol) and 5-bromo-2-nitropyridine (0.170 g, 0.836 mmol) in DMSO (2.5 mL) at room temperature. The mixture was stirred at room temperature for 2 hours and then at 60° C. for 24 hours. The reaction mixture was partitioned between EtOAc and 2M aqueous HCl ensuring the water layer was acidic. The organic layer was separated and washed further with citric acid, water and brine, then dried over magnesium sulfate, filtered, evaporated in vacuo and triturated in diethyl ether to yield the title compound (0.180 g, 60%):

Workup

  1. waitat 60° C. for 24 hours
  2. customThe reaction mixture was partitioned between EtOAc and 2M aqueous HCl ensuring the water layer
  3. customThe organic layer was separated
  4. washwashed further with citric acid, water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customtriturated in diethyl ether

Sources & evidence

ORD record
ord-84bfbdc7f1c34a1f89d326dfcb32db1b
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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