Sodium hydride → HCID 86663364, compound

HRID 1623558Notes

Reaction equation

HRID 1623558 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[Br:9][C:10]1[CH:11]=[C:12]([CH:16]=[O:17])[CH:13]=[N:14][CH:15]=1>CS(C)=O>[Br:9][C:10]1[CH:15]=[N:14][CH:13]=[C:12]([CH:16]2[CH2:2][O:17]2)[CH:11]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 27847345-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 86663364HCID 86663364, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of trimethylsulfoxonium iodide (CAS#1774-47-6, 11.83 g, 53.8 mmol) in methyl sulfoxide (80 mL), was added slowly sodium hydride (60% dispersion in oil, 1.989 g, 49.7 mmol). The reaction was permitted to stir for 15 min at room temperature. A solution of 5-bromo-pyridine-3-carbaldehyde (CAS#135124-70-8, 5.0 g, 26.9 mmol) in dimethylsulfoxide (20 mL) was added slowly to the reaction mixture. The reaction permitted to stir for 10 minutes after the addition was complete. The reaction was cooled to 0° C., quenched with brine, and diluted with diethyl ether. The layers were separated and the aqueous layer was extracted two additional times with diethyl ether. The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 0 to 60%) to afford 3-bromo-5-oxiranyl-pyridine; MS: (ES+) m/z 200.0 (M+H)+.

Workup

  1. stirringto stir for 10 minutes
  2. additionafter the addition
  3. temperatureThe reaction was cooled to 0° C.
  4. customquenched with brine
  5. additiondiluted with diethyl ether
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted two additional times with diethyl ether
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 0 to 60%)

Sources & evidence

ORD record
ord-581a2d5e915746b0b6e2f727c584fe7b
Source dataset
uspto-grants-2014_07
Patent number
US08778972B2

Reaction notes

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