1,2-Dibromoethane → HCID 21084117, compound

HRID 347838Notes

Reaction equation

HRID 347838 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:12]=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1.C([Li])CCC.[Br:18]CCBr.[Cl-].[NH4+]>O1CCCC1.O>[CH3:1][O:2][CH2:3][C:4]1[CH:12]=[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([Br:18])[N:6]2[N:5]=1

Participants

7

Reactant 4

HCID 78391,2-DibromoethaneHCID 25517Ammonium ChlorideHCID 210841002-(Methoxymethyl)pyrazolo[1,5-a]pyridineHCID 178418339Butyllithium

Product 1

HCID 21084117HCID 21084117, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(methoxymethyl)pyrazolo[1,5-a]pyridine (3.5 g) dissolved in tetrahydrofuran (350 mL) was added n-butyllithium (2.66M hexane solution; 10.5 mL) dropwise at −78° C. under a nitrogen stream, and the reaction mixture was stirred for 30 minutes. 1,2-Dibromoethane (2.05 mL) was added dropwise to the obtained reaction mixture and stirring was continued for 30 minutes. After adding saturated aqueous ammonium chloride to the reaction mixture, the temperature was raised to room temperature, water was added and extraction was performed with ethyl acetate. The organic extract was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography and the title compound (2.75 g) was obtained as a light yellow oil from the n-hexane:ethyl acetate (10:1) fraction.

Workup

  1. stirringstirring
  2. waitwas continued for 30 minutes
  3. extractionextraction
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-56e621e3414245d497620296b37fa609
Source dataset
uspto-grants-2007_02
Patent number
US07176216B2

Reaction notes

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