Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Hydrazine | HCID 9321 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 59834372 | HCID 59834372 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 59834389 | HCID 59834389 | 5.7% |
Reaction Steps
[5-(2,4-Difluoro-phenoxy)-3-fluoro-pyridin-2-yl]-(2-methoxy-phenyl)-methanone (560 mg, 1.5 mmol) was added to 17 mL of EtOH and the reaction mixture was heated until all solid had dissolved. The reaction mixture was cooled, and (N,N-diisopropyl)ethylamine (0.21 mL, 2.3 mmol) and hydrazine (0.1 mL, 3.1 mmol) were added. The reaction mixture was stirred for four hours at room temperature, and then was taken up in 60 mL of EtOAc, washed four times with 20 mL of water, dried (MgSO4). The organic solvent was filtered and concentrated under reduced pressure. The residue was purified by flash chromatography 40 mm×7.5 cm) with 4: to 1:1 hexanes/EtOAc to yield 0.03 g of 6-(2,4-difluoro-phenoxy)-3-(2-methoxy-phenyl)-1H-pyrazolo[4,3-b]pyridine. Mass Spec. M+H=354. Mp: 143.2-144.9° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07566708B2 |
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| Source dataset | uspto-grants-2009_07 |
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| ORD ID | ord-14d18218cc87428dbfef49dbc6d4f522 |
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| Source note | uspto-grants-2009_07 |
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