Methyl iodide → N-((5-bromopyridin-3-yl)(cyclopropyl)methyl)-N-methylethanesulfonamide

HRID 391319Notes

Reaction equation

HRID 391319 reaction equation
IC.[Br:3][C:4]1[CH:5]=[C:6]([CH:10]([CH:17]2[CH2:19][CH2:18]2)[NH:11][S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])[CH:7]=[N:8][CH:9]=1.[C:20](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O.O>[Br:3][C:4]1[CH:5]=[C:6]([CH:10]([CH:17]2[CH2:19][CH2:18]2)[N:11]([CH3:20])[S:12]([CH2:15][CH3:16])(=[O:13])=[O:14])[CH:7]=[N:8][CH:9]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59578386N-((5-bromopyridin-3-yl)(cyclopropyl)methyl)ethanesulfonamide

Product 1

HCID 59578387N-((5-bromopyridin-3-yl)(cyclopropyl)methyl)-N-methylethanesulfonamideYield 15.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Iodomethane (0.059 mL, 0.940 mmol) was added to a mixture of N-((5-bromopyridin-3-yl)(cyclopropyl)methyl)ethanesulfonamide (200 mg, 0.627 mmol) and potassium carbonate (130 mg, 0.940 mmol) in DMF (6 mL) at room temperature. The resulting mixture was heated at 60° C. for 24 h. The reaction mixture was diluted with EtOAc and water, and the mixture was washed with H2O and brine. The organic layer was separated and dried over anhydrous Na2SO4. After filtration and concentration, the residue was purified by flash column to give 32 mg of N-((5-bromopyridin-3-yl)(cyclopropyl)methyl)-N-methylethanesulfonamide. ESI-MS: m/z 334.9 (M+H)+.

Workup

  1. washthe mixture was washed with H2O and brine
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationAfter filtration and concentration
  5. customthe residue was purified by flash column

Sources & evidence

ORD record
ord-593ae9f600454f26ba4c0b00f5efd930
Source dataset
uspto-grants-2013_02
Patent number
US08383827B2

Reaction notes

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