Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | HCID 89876340 | HCID 89876340 | — |
| Catalyst | (2',4'-Diisopropyl-3-methoxy-6-methyl-6'-propyl-2-biphenylyl)[bis(2-methyl-2-propanyl)]phosphine | HCID 56641709 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 89876291 | HCID 89876291 | 66% |
Reaction Steps
6-bromo-4-(2,3-dichloroindol-1-yl)-5-methoxy-2-methyl-pyridazin-3-one (0.200 g, 0.496 mmol), Pd2Cl2(allyl)2 (2.7 mg, 0.00744 mmol), ditert-butyl-[6-methoxy-3-methyl-2-(2,4,6-triisopropylphenyl)phenyl]phosphane (11.6 mg, 0.0248 mmol) and dicesium carbonate (0.243 g, 0.744 mmol) are suspended in toluene (3 mL) and methanol (60 μL). The resulting reaction mixture is heated under microwave irradiation to 110° C. for 20 min. The resulting reaction mixture is filtered, washing with EtOAc and concentrated under reduced pressure onto silica. Purification by flash chromatography (combiflash, 0 to 30% EtOAc/isohexane) afforded the desired product 4-(2,3-dichloroindol-1-yl)-5,6-dimethoxy-2-methyl-pyridazin-3-one (0.116 g, 0.3275 mmol, 66% yield) as a brown oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09049864B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-454c3996c63c4682b517fac75647134e |
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| Source note | uspto-grants-2015_06 |
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