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

HRID 1774767Notes

Reaction equation

HRID 1774767 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:9][S:10]([CH2:13][CH3:14])(=[O:12])=[O:11])[CH:5]=[N:6][CH:7]=1.[H-].[Na+].[CH3:17]I>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]([CH3:17])[S:10]([CH2:13][CH3:14])(=[O:11])=[O:12])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58215658N-((5-bromopyridin-3-yl)methyl)ethanesulfonamide

Product 1

HCID 66788309N-((5-Bromopyridin-3-yl)methyl)-N-methylethanesulfonamideYield 94.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethanesulfonic acid (5-bromo-pyridin-3-ylmethyl)-amide (intermediate A-11, 0.21 g, 0.752 mmol) in DMF (6 mL) cooled at 0° C. with an ice bath was added 60% NaH in mineral oil (0.039 g, 0.98 mmol) and the mixture was stirred for 15 min. Then, MeI (0.136 g, 0.96 mmol) was added and the reaction was stirred at 0° C. for another 15 min before being quenched with aq. ammonia (2 mL). The mixture was further diluted with brine and then extracted with EtOAc (2×15 mL). Combined organics were dried over Na2SO4, filtered and evaporated to dryness to give the title compound (0.209 g, 85%) as a yellow oil which was used with no further purification. MS: 293.1 and 295.1 (M+H+).

Workup

  1. stirringthe reaction was stirred at 0° C. for another 15 min
  2. custombefore being quenched with aq. ammonia (2 mL)
  3. additionThe mixture was further diluted with brine
  4. extractionextracted with EtOAc (2×15 mL)
  5. dry with materialCombined organics were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-1c8a6c8d9db449cc864fd3bcb4e32307
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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