HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 137133009, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 3,4-dihydro-2H-pyran | HCID 8080 | — |
| Reactant | p-Toluenesulfonic acid monohydrate | HCID 521998 | — |
| Reactant | HCID 178497271 | HCID 178497271 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 137133009 | HCID 137133009 | 70% |
Reaction Steps
A mixture of 3-cyclopropyl-6-(4-hydroxy-phenyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid methyl ester (12.9 g), 3,4-dihydro-2H-pyran (5.26 g) and p-toluenesulfonic acid monohydrate (2.38 g) in THF (300 mL) was stirred at r.t. until the reaction was complete. Water was added and the mixture was extracted with ethyl acetate, the combined organic phases were washed with water and brine, dried over magnesium sulfate and concentrated. The residue was chromatographed over a short path column (heptane/ethyl acetate gradient). 11.4 g (70%) of the title compound were obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09133181B2 |
| Source dataset | uspto-grants-2015_09 |
| ORD ID | ord-5014953efef94ff2829a0c58e6c010fe |
| Source note | uspto-grants-2015_09 |