Sodium hydride → 3-(Pyrazolo[1,5-a]pyrid-4-yloxy)-1,2-epoxypropane

HRID 1590114Notes

Reaction equation

HRID 1590114 reaction equation
[H-].[Na+].[OH:3][C:4]1[C:5]2[N:6]([N:10]=[CH:11][CH:12]=2)[CH:7]=[CH:8][CH:9]=1.S(C1C=CC(C)=CC=1)(O[CH2:17][CH:18]1[O:20][CH2:19]1)(=O)=O.[NH4+].[Cl-]>CCOCC.O.CN(C=O)C>[N:10]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:4]([O:3][CH2:17][CH:18]3[O:20][CH2:19]3)[C:5]2=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 160868Glycidyl tosylateHCID 15257896Pyrazolo(1,5-a)pyridin-4-ol

Product 1

HCID 152578983-(Pyrazolo[1,5-a]pyrid-4-yloxy)-1,2-epoxypropane

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

NaH (containing 60% of oil, 270 mg, 4.5 mmole) was washed with anhydrous petroleum ether, and was admixed, under atmosphere of argon gas, with distilled DMF (15 ml) and 4-hydroxypyrazolo[1,5-a]pyridine (5) (402 mg, 3.0 mmole), followed by stirring for 30 min to give a light pink suspension. Subsequently, glycidyl tosylate (821 mg, 3.6 mmole) was added to the suspension, followed by stirring overnight under atmosphere of argon gas to obtain a red-yellow suspension. The reaction mixture was neutralized by adding about 10 ml of saturated aqueous NH4Cl, followed by addition of water (20 ml) and extraction with ether. The extract was washed with water, dried and freed of the solvent by distillation, and the residue was purified on a column of silica gel (7734, chloroform).

Workup

  1. customto give a light pink suspension
  2. stirringby stirring overnight under atmosphere of argon gas
  3. customto obtain a red-yellow suspension
  4. washThe extract was washed with water
  5. customdried
  6. distillationfreed of the solvent by distillation
  7. customthe residue was purified on a column of silica gel (7734, chloroform)

Sources & evidence

ORD record
ord-5a9b9155dba44199bab05719e34f82b7
Source dataset
uspto-grants-1993_04
Patent number
US05202334

Reaction notes

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