Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 3-Fluorophenol | HCID 9743 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 58168117 | HCID 58168117 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58168077 | HCID 58168077 | 91% |
Reaction Steps
9-Fluoro-5H-benzo[c][1,8]naphthyridin-6-one (40 mg, 0.19 mmol), 3-fluorophenol (63 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, washed with H2O, and dried under vacuum to provide 77 (52 mg, 91% yield) as a tan solid. LC-MS (M+H=307, obsd.=307). 1H NMR (400 MHz, d6-DMSO): δ 12.00 (s, 1H), 8.77 (dd, 1H), 8.51 (dd, 1H), 8.36 (d, 1H), 8.21 (d, 1H), 7.50 (t, 1H), 7.30 (m, 2H), 7.09 (m, 2H), 7.02 (dd, 1H).
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-1ff1648cc9c848d390d5772e44bef44b |
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| Source note | uspto-grants-2014_05 |
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