Triethylamine → 7-Methoxy-4-propionyl-2-trifluoromethyl-pyrazolo[1,5-a]pyridine

HRID 2357911Notes

Reaction equation

HRID 2357911 reaction equation
[OH:1][CH:2]([C:5]1[C:6]2[N:7]([N:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=2)[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1)[CH2:3][CH3:4].C(N(CC)CC)C>CS(C)=O>[CH3:12][O:11][C:8]1[N:7]2[N:13]=[C:14]([C:16]([F:19])([F:17])[F:18])[CH:15]=[C:6]2[C:5]([C:2](=[O:1])[CH2:3][CH3:4])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 593893854-(1-Hydroxypropyl)-7-methoxy-2-trifluoromethyl-pyrazolo[1,5-a]pyridine

Product 1

HCID 593893617-Methoxy-4-propionyl-2-trifluoromethyl-pyrazolo[1,5-a]pyridineYield 75.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The compound of Example 135 (32.1 g) was dissolved in DMSO (780 mL) in an argon atmosphere. To this solution, triethylamine (163 mL) and sulfur trioxide-pyridine complex (93.1 g) were sequentially added and the mixture was stirred at room temperature for 1 hour. The reaction mixture was then poured into ice water and the resulting solid product was collected by filtration. The product was washed with water and dissolved in ethyl acetate. The solution was dried over anhydrous sodium sulfate. Evaporation of the solvent afforded the title compound as a colorless powder (24.0 g).

Workup

  1. filtrationthe resulting solid product was collected by filtration
  2. washThe product was washed with water
  3. dissolutiondissolved in ethyl acetate
  4. dry with materialThe solution was dried over anhydrous sodium sulfate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-565902a8da2043ef8f0bd277bd280e60
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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