Sodium hydride → HCID 121386233, compound

HRID 2203015Notes

Reaction equation

HRID 2203015 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[N:6][CH:7]=1.[H-].[Na+].Br[CH:22]([CH3:28])[C:23]([CH:25]1[CH2:27][CH2:26]1)=[O:24]>CN(C=O)C>[Br:1][C:2]1[N:3]=[CH:4][C:5](=[N:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[N:6]([CH:22]([CH3:28])[C:23]([CH:25]2[CH2:27][CH2:26]2)=[O:24])[CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 450808052-Bromo-1-cyclopropylpropan-1-oneHCID 57749444HCID 57749444, compound

Product 1

HCID 121386233HCID 121386233, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(5-bromopyrazin-2-yl)-4-methylbenzenesulfonamide (1.73 g) in DMF (20 ml) was added NaH (60% in oil, 0.316 g) at 0° C., and the mixture was stirred at room temperature for 30 min. To the mixture was added 2-bromo-1-cyclopropylpropan-1-one (1.87 g) at room temperature, and the mixture was stirred overnight. The mixture was partitioned between EtOAc and water, and the organic layer was washed with brine, dried over MgSO4, concentrated in vacuo, and purified by silica gel column chromatography (hexane/EtOAc) to give the title compound (1.02 g) as a solid.

Workup

  1. stirringthe mixture was stirred overnight
  2. customThe mixture was partitioned between EtOAc and water
  3. washthe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. custompurified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-90018ebbe19c46ebba75d64ac018ace1
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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