HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 4-Hydroxymethyl-7-iodo-2-trifluoromethylpyrazolo[1,5-a]pyridin
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | TBAF tetrahydrofuran | HCID 11078149 | — |
| Reactant | 4-(t-Butyldimethylsilyloxymethyl)-7-iodo-2-trifluoromethylpyrazolo[1,5-a]pyridine | HCID 58014015 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-Hydroxymethyl-7-iodo-2-trifluoromethylpyrazolo[1,5-a]pyridin | HCID 59389356 | 95.2% |
Reaction Steps
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).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07763617B2 |
| Source dataset | uspto-grants-2010_07 |
| ORD ID | ord-2182e7a5147f4fbda759c941b72298b4 |
| Source note | uspto-grants-2010_07 |