Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-fluoro-2-methyl-1H-indol-5-ol | HCID 10352036 | — |
| Reactant | HCID 22646547 | HCID 22646547 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59712239 | HCID 59712239 | 35.1% |
Reaction Steps
A suspension of 4-chloro-6-cyano-7-methoxyquinoline (200 mg, 0.91 mmol), (prepared as described for the starting material in Example 1), 4-fluoro-5-hydroxy-2-methylindole (181 mg, 1.1 mmol), (prepared as described for the starting material in Example 11), and cesium carbonate (444 mg, 1.36 mmol) in DMF (6 ml) was heated at 95° C. for 2.5 hours. After cooling, the mixture was filtered, the filtrate was evaporated under vacuum and the residue was purified by column chromatography eluting with methylene chloride, followed by methanol/ethyl acetate/methylene chloride (2/10/88 followed by 5/15/80) to give 6-cyano-4-(4-fluoro-2-methylindol-5-yloxy)-7-methoxyquinoline (111 mg, 35%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07371765B2 |
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| Source dataset | uspto-grants-2008_05 |
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| ORD ID | ord-ec3d4961d8734d108f188170f871e810 |
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| Source note | uspto-grants-2008_05 |
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