Sodium hydride → HCID 18510272, compound

HRID 1371045Notes

Reaction equation

HRID 1371045 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:18])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][CH:11]=2)[CH:5]=[N:6][CH:7]=1.[H-].[Na+].[CH2:21](Br)[CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:18])[CH:9]([C:10]2[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][CH:11]=2)[CH2:21]/[CH:22]=[CH:23]/[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 98116BromomethylstyreneHCID 18510222HCID 18510222, compound

Product 1

HCID 18510272HCID 18510272, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1-(5-bromo-3-pyridinyl)-2-[4-(methylsulfanyl)phenyl]-1-ethanone in DMF (2.5 mL) at 0° C. was added NaH (15 mg, 0.5 mmole). The reaction was stirred 30 minutes, at which point cinnamyl bromide (0.1 g, 0.5 mmole) was added and the reaction was allowed to warm to room temperature. The reaction was quenched with H2O and extracted with ethyl acetate. The organic phase was dried (Na2SO4), filtered, and evaporated to give the title compound.

Workup

  1. additionwas added
  2. customThe reaction was quenched with H2O
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-6af79293ac3740d7b1e501e0d56e5bce
Source dataset
uspto-grants-2003_06
Patent number
US06583126B2

Reaction notes

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