Benzenesulfonyl chloride → HCID 67953948, compound

HRID 1916860Notes

Reaction equation

HRID 1916860 reaction equation
[CH3:1][C:2]1[N:6]2[CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19].[H-].[Na+].[C:25]1([S:31](Cl)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C>[C:18]([O:17][C:16]([N:15]([C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][C:8]([C:11]([F:13])([F:12])[F:14])=[CH:7][N:6]2[C:2]=1[CH3:1])[S:31]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:33])=[O:32])=[O:22])([CH3:19])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 67976467HCID 67976467, compound

Product 1

HCID 67953948HCID 67953948, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound 10-E (0.063 g, 0.2 mmol) in DMF (1 mL) at 0° C. was added 95% NaH (0.012 g, 0.5 mmol) and the reaction mixture was stirred for 10 minutes. Benzenesulfonyl chloride (0.053 g, 0.3 mmol) was added and the reaction mixture was stirred at room temperature overnight. The reaction was quenched by the addition of H2O and the solution was extracted with ethyl acetate. After separation of the organic and aqueous layers a sufficient amount of water was added to remove any dissolved DMF from the organic layer. The organic layer was dried over Na2SO4, filtered, and the solvent evaporated under reduced pressure to afford the crude product. The crude material was purified by flash column chromatography, eluting with a hexanes-EtOAc gradient to give compound 10-F as a white solid (0.066 g, 72%); MS m/z (M+H+) 456.

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. customThe reaction was quenched by the addition of H2O
  3. extractionthe solution was extracted with ethyl acetate
  4. customAfter separation of the organic and aqueous layers a sufficient amount of water
  5. additionwas added
  6. customto remove any dissolved DMF from the organic layer
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. customthe solvent evaporated under reduced pressure
  10. customto afford the crude product
  11. customThe crude material was purified by flash column chromatography
  12. washeluting with a hexanes-EtOAc gradient

Sources & evidence

ORD record
ord-c0652215de94465f875977a1b0685bd6
Source dataset
uspto-grants-2013_12
Patent number
US08618150B2

Reaction notes

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