Potassium Hydroxide → 2-Isopropyl-3-cyclopentylcarbonylpyrazolo[1,5-a]pyridine

HRID 483085Notes

Reaction equation

HRID 483085 reaction equation
[CH:1]([C:4]1[CH:12]=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2].[CH:13]1([C:18](Cl)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14]1.[OH-].[K+]>>[CH:1]([C:4]1[C:12]([C:18]([CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:19])=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 14797Potassium HydroxideHCID 78284Cyclopentanecarbonyl chlorideHCID 113786582-Isopropylpyrazolo[1,5-a]pyridine

Product 1

HCID 133917202-Isopropyl-3-cyclopentylcarbonylpyrazolo[1,5-a]pyridine

Conditions

Temperature
160 °C

Procedure

A mixture of 5 g of 2-isopropylpyrazolo[1,5-a]pyridine and 5 ml of cyclopentylcarbonyl chloride was heated at 160° C. for 4.5 hours and, after cooling, poured into aqueous potassium hydroxide solution. The mixture was extracted with dichloromethane and the organic layer was dried over anhydrous sodium sulfate, concentrated to dryness. The residue was applied to a column of silica gel, eluting with ethyl acetate-hexane(1:9), to give 2.1 g of the title compound as colorless crystals, mp 106°-110° C.

Workup

  1. temperatureafter cooling
  2. extractionThe mixture was extracted with dichloromethane
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated to dryness
  5. washeluting with ethyl acetate-hexane(1:9)

Sources & evidence

ORD record
ord-6f0cd25f1297408f9fdeaad19dcb09fa
Source dataset
uspto-grants-1986_03
Patent number
US04578392

Reaction notes

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