Methyl iodide → N-(2-Bromo-pyridin-3-yl)-4-fluoro-N-methyl-benzenesulfonamide

HRID 1716282Notes

Reaction equation

HRID 1716282 reaction equation
[Br:1][C:2]1[C:7]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:19]([O-])([O-])=O.[Cs+].[Cs+].IC>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[C:7]([N:8]([CH3:19])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 86619934N-(2-Bromo-pyridin-3-yl)-4-fluoro-benzenesulfonamide

Product 1

HCID 86619935N-(2-Bromo-pyridin-3-yl)-4-fluoro-N-methyl-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(2-bromo-pyridin-3-yl)-4-fluoro-benzenesulfonamide (0.3 g, 0.9 mmol) from Step A in DMF (4 ml) was added Cs2CO3 (0.4 g, 1.3 mmol). To the mixture iodomethane (0.128 ml, 2 mmol) was added at room temperature. The mixture was stirred for 5 hours and then was diluted with EtOAc and washed with saturated NaCl solution. The organic phase was dried over sodium sulfate and concentrated. The crude was purified through Chromatography. (3-4% EtOAc in dichloromethane). MS 344.9 (M+H)+

Workup

  1. washwashed with saturated NaCl solution
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe crude was purified through Chromatography

Sources & evidence

ORD record
ord-b0fcd8dbdc56448a835c3b1e8816b0e2
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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