Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 3-Methoxyphenol | HCID 9007 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 58168117 | HCID 58168117 | — |
| Product | HCID 58168240 | HCID 58168240 | 37% |
Reaction Steps
9-Fluoro-5H-benzo[c][1,8]naphthyridin-6-one (40 mg, 0.19 mmol), 3-methoxyphenol (70 mg, 0.56 mmol), and potassium carbonate (129 mg, 0.93 mmol) were suspended in DMF (1.5 mL), and stirred for 20 minutes at 180° C. in the microwave. The reaction mixture was quenched with H2O. The resulting precipitate was filtered and washed with H2O. The precipitate was triturated with MeOH, filtered, washed with MeOH, and dried under vacuum to provide 76 (22 mg, 37% yield) as a brown solid. LC-MS (M+H=319, obsd.=319). 1H NMR (400 MHz, d6-DMSO): δ 11.99 (s, 1H), 8.73 (dd, 1H), 8.50 (dd, 1H), 8.32 (d, 1H), 8.14 (d, 1H), 7.38 (t, 1H), 7.30 (dd, 1H), 7.22 (dd, 1H), 6.83 (dd, 1H), 6.77 (t, 1H), 6.71 (dd, 1H), 3.77 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08735584B2 |
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| Source dataset | uspto-grants-2014_05 |
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| ORD ID | ord-0804b5166b674ec98adb86c3ee2898bb |
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| Source note | uspto-grants-2014_05 |
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