Iodoethane → HCID 86679141, compound

HRID 1774768Notes

Reaction equation

HRID 1774768 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+].I[CH2:18][CH3:19]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]([CH2:18][CH3:19])[S:10]([CH2:13][CH3:14])(=[O:11])=[O:12])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 58215658N-((5-bromopyridin-3-yl)methyl)ethanesulfonamide

Product 1

HCID 86679141HCID 86679141, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethanesulfonic acid (5-bromo-pyridin-3-ylmethyl)-amide (intermediate A-11, 0.051 g, 0.182 mmol) in DMF (3 mL) cooled at 0° C. with an ice bath was added 60% NaH in mineral oil (0.011 g, 0.274 mmol) and the mixture was stirred at room temperature for 20 min. Then, iodoethane (0.045 g, 0.292 mmol) was added and the reaction mixture was stirred for 3 h before being quenched with water (5 mL). The aqueous solution was extracted with EtOAc (2×15 mL). Combined organics were dried over Na2SO4, filtered and evaporated to dryness to give the title compound (0.051 g, 82%) as orange oil which was used with no further purification. MS: 307.1 and 309.2 (M+H+).

Workup

  1. stirringthe reaction mixture was stirred for 3 h
  2. custombefore being quenched with water (5 mL)
  3. extractionThe aqueous solution was extracted with EtOAc (2×15 mL)
  4. dry with materialCombined organics were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-632381c456714a13bdfb3ececdd4e16d
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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