Water → 4-Hydroxymethyl-7-iodo-2-trifluoromethylpyrazolo[1,5-a]pyridin
Reaction equation
[Si]([O:8][CH2:9][C:10]1[C:11]2[N:12]([N:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=2)[C:13]([I:16])=[CH:14][CH:15]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.O>O1CCCC1>[F:23][C:20]([F:21])([F:22])[C:18]1[CH:19]=[C:11]2[C:10]([CH2:9][OH:8])=[CH:15][CH:14]=[C:13]([I:16])[N:12]2[N:17]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The compound of Example 92 (4.57 g) was dissolved in tetrahydrofuran (50.0 mL). While this solution was chilled in an ice bath, 1.0 mol/L tetran-butyl ammonium fluoride/tetrahydrofuran solution (12.0 mL) was added and the mixture was stirred at room temperature for 1 hour. Subsequently, water was added and the reaction mixture was extracted with ethylacetate. The organic layer was washed sequentially with water and saturated brine and dried over anhydrous sodium sulfate. Evaporation of the solvent and subsequent purification of the residue by silica gel column chromatography (hexane:ethyl acetate=2:1) afforded the title compound as a pale yellow powder (3.26 g).
Workup
- temperatureWhile this solution was chilled in an ice bath
- extractionthe reaction mixture was extracted with ethylacetate
- washThe organic layer was washed sequentially with water and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customEvaporation of the solvent and subsequent purification of the residue by silica gel column chromatography (hexane:ethyl acetate=2:1)
Sources & evidence
- ORD record
- ord-2182e7a5147f4fbda759c941b72298b4
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07763617B2
Reaction notes
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