p-Anisoyl chloride → HCID 13636551, compound

HRID 731707Notes

Reaction equation

HRID 731707 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].[CH3:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1.[Al+3].[Cl-].[Cl-].[Cl-].[OH-].[K+]>C(OCC)C>[CH:1]([C:4]1[C:12]([C:19]([C:18]2[CH:22]=[CH:23][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)=[O:20])=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 7477p-Anisoyl chlorideHCID 14797Potassium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 113786582-Isopropylpyrazolo[1,5-a]pyridine

Product 1

HCID 13636551HCID 13636551, compoundYield 13.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3.2 ml of 2-isopropylpyrazolo[1,5-a]pyridine, 2.2 g of 4-methoxybenzoyl chloride and 200 mg anhydrous AlCl3 were mixed with stirring at room temperature for 4 days. After cooling, 50 ml of ethyl ether was added to the mixture, followed by addition of 4N KOH solution to pH 8-8.5 at 0-5° C. The mixture was extracted with ethyl acetate twice. The combined organic phases were washed with brine and dried over MgSO4. The ethyl acetate was evaporated under reduced pressure to obtain 6.4 g of crude product, which was purified on an aluminum oxide column with hexane-dichloromethane-ethyl acetate as eluant to yield 510 mg (13.6%) of (2-isopropylpyrazolo[1,5-a]pyridin-3-yl)(4-methoxyphenyl)methanone. Compound 1008.

Workup

  1. temperatureAfter cooling
  2. extractionThe mixture was extracted with ethyl acetate twice
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over MgSO4
  5. customThe ethyl acetate was evaporated under reduced pressure
  6. customto obtain 6.4 g of crude product, which
  7. customwas purified on an aluminum oxide column with hexane-dichloromethane-ethyl acetate as eluant

Sources & evidence

ORD record
ord-711fb5db6f6749e09aea1bad3c583788
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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