Sodium hydride → N-(3-Chloro-4-(4-methylpyridin-3-yl)phenyl)methanesulfonamide

HRID 1405090Notes

Reaction equation

HRID 1405090 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[CH3:15])[NH2:5].[CH3:16][S:17](Cl)(=[O:19])=[O:18].[H-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][S:17]([CH3:16])(=[O:19])=[O:18])[CH:6]=[CH:7][C:8]=1[C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[CH3:15]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 667144823-Chloro-4-(4-methylpyridin-3-yl)aniline

Product 1

HCID 56655075N-(3-Chloro-4-(4-methylpyridin-3-yl)phenyl)methanesulfonamideYield 3.54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Intermediate 27 (0.102 g, 0.466 mmol) and methanesulfonyl chloride (0.043 mL, 0.560 mmol) in DMF (3.26 mL) was added sodium hydride (0.037 g, 0.933 mmol) at room temperature. The reaction mixture was allowed to stir at room temperature for 3 days, then quenched with saturated aqueous NH4Cl solution and diluted with EtOAc. The layers were separated and the aqueous phase was extracted with EtOAc (5×). The organic phases were combined, dried over Na2SO4, filtered, and concentrated to afford a yellow residue, which was further dried under high vacuum. The crude material was dissolved in CH2Cl2 and purified by silica gel chromatography using an ISCO machine (12 g column, 30 mL/min, 0-10% MeOH in CH2Cl2 over 25 min, tr=14 min) to afford the title compound (5.1 mg, 0.016 mmol, 3.54% yield) as a white solid.

Workup

  1. customquenched with saturated aqueous NH4Cl solution
  2. additiondiluted with EtOAc
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with EtOAc (5×)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a yellow residue, which
  9. customwas further dried under high vacuum
  10. dissolutionThe crude material was dissolved in CH2Cl2
  11. custompurified by silica gel chromatography
  12. customan ISCO machine (12 g column, 30 mL/min, 0-10% MeOH in CH2Cl2 over 25 min, tr=14 min)

Sources & evidence

ORD record
ord-c864144a50714c429a5f41b781f499ec
Source dataset
uspto-grants-2014_12
Patent number
US08916553B2

Reaction notes

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