Water → N-(5-bromo-2-chloropyridin-3-yl)-N-methylmethanesulfonamide

HRID 241050Notes

Reaction equation

HRID 241050 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])[C:5]([Cl:8])=[N:6][CH:7]=1.[C:14](=O)([O-])[O-].[K+].[K+].IC.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([N:9]([CH3:14])[S:10]([CH3:13])(=[O:12])=[O:11])[C:5]([Cl:8])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59519513N-(5-bromo-2-chloro-3-pyridinyl)methanesulfonamide

Product 1

HCID 86647824N-(5-bromo-2-chloropyridin-3-yl)-N-methylmethanesulfonamideYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(5-bromo-2-chloropyridin-3-yl)methanesulfonamide (96 mg, 0.34 mmol, reagent preparation 24) in DMF (1 mL) was treated with potassium carbonate (93 mg, 0.68 mmol) and iodomethane (33 uL, 0.51 mmol) at rt for 18 h. Water was then added, and the resulting aqueous mixture was extracted twice with ethyl acetate. The combined organic extracts were washed with aqueous lithium chloride (10%) followed by water, dried over magnesium sulfate, filtered, and concentrated in vacuo to provide N-(5-bromo-2-chloropyridin-3-yl)-N-methylmethanesulfonamide (91.2 mg, 0.304 mmol, 90% yield) as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.46 (d, 1H), 8.00 (d, 1H), 3.32 (s, 3H), 3.07 (s, 3H); MS (EI) for C7H8BrClN2O2S: 299, 301, 303 (Br+Cl isotopes, MH+).

Workup

  1. extractionthe resulting aqueous mixture was extracted twice with ethyl acetate
  2. washThe combined organic extracts were washed with aqueous lithium chloride (10%)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ae72cbfbfd894e9386653e91f9bb230c
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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