HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 1-(2,2-Difluoroethyl)-3-{4-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]phenyl}-1H-pyrazolo[4,3-b]pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 3-Methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine | HCID 58577371 | — |
| Reactant | 4-(1-(2,2-difluoroethyl)-1H-pyrazolo[4,3-b]pyridin-3-yl)phenol | HCID 136409091 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 1-(2,2-Difluoroethyl)-3-{4-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]phenyl}-1H-pyrazolo[4,3-b]pyridine | HCID 56648019 | 42.9% |
Reaction Steps
To a stirred solution of 4-[1-(2,2-difluoroethyl)-1H-pyrazolo[4,3-b]pyridin-3-yl]phenol (142 mg) in DMF (4 mL) was added NaH (60% in oil, 20.63 mg) at room temperature. The mixture was stirred at room temperature for 30 min and then 3-methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine (109 mg) was added. The mixture was exposed to microwave irradiation at 180° C. for 30 min, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane). The product was crystallized from AcOEt/hexane to give the title compound (90 mg)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09029536B2 |
| Source dataset | uspto-grants-2015_05 |
| ORD ID | ord-471eeab7bb9a4a52a8b9fb54944672d4 |
| Source note | uspto-grants-2015_05 |