Benzenesulfonamide, N,4-dimethyl- → N-(6-chloropyridin-2-yl)-N,4-dimethylbenzenesulfonamide

HRID 2077504Notes

Reaction equation

HRID 2077504 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4].[H-].[Na+].Cl[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[N:17]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C(Cl)Cl.C([O-])(O)=O.[Na+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[Cl:22][C:18]1[N:17]=[C:16]([N:2]([CH3:1])[S:3]([C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=2)(=[O:5])=[O:4])[CH:21]=[CH:20][CH:19]=1

Participants

9

Reactant 4

HCID 12543Benzenesulfonamide, N,4-dimethyl-HCID 169892,6-DichloropyridineHCID 24758Sodium hydrideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

Product 1

HCID 57585115N-(6-chloropyridin-2-yl)-N,4-dimethylbenzenesulfonamideYield 33.7%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
100 °C

Procedure

N-Methyl-p-toluenesulfonamide (0.2 g, 1 mmol) was added to a microwave vial equipped with a stir bar. DMF (3 mL) was added to the mixture, followed by NaH (0.13 g, 5.40 mmol), and the reaction solution was allowed to stir for 20 minutes. Then 2,6-dichloropyridine (0.24 g, 1.6 mmol), palladium(II) acetate (0.0242 g, 0.108 mmol) and Xantphos (0.024 g) were added to the mixture. The vial was capped and placed in the CEM microwave and heated for 10 minutes at 100° C. The mixture was diluted with DCM and saturated NaHCO3. The aqueous layer was extracted with 4:1 DCM/MeOH three times, and the combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude was purified by silica gel chromatography (1-10% EtOAc/hexanes) to give N-(6-chloropyridin-2-yl)-N,4-dimethylbenzenesulfonamide (0.1 g, 31.2% yield) as a colorless oil. MS (ESI pos. ion) m/z: 297 (MH+). Calculated exact mass for C13H13ClN2O2S: 296.

Workup

  1. customvial equipped with a stir bar
  2. customThe vial was capped
  3. extractionThe aqueous layer was extracted with 4:1 DCM/MeOH three times
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude was purified by silica gel chromatography (1-10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ec1ee15e66984335a61881f26d68cd65
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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