Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 4-Fluorophenol | HCID 9732 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one | HCID 58168008 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58167957 | HCID 58167957 | 21% |
Reaction Steps
1-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (50 mg, 0.22 mmol), 4-fluorophenol (73 mg, 0.65 mmol), and potassium carbonate (150 mg, 1.08 mmol) were suspended in DMF (2 mL), and stirred overnight at 100° C. The reaction solution was cooled to room temperature, diluted with H2O, and the resulting precipitate was filtered. The precipitate was washed with H2O, and dried under vacuum to provide 149 (14 mg, 21% yield) as a tan solid. LC-MS (M+H=307, obsd.=307). 1H NMR (400 MHz, d6-DMSO): δ 12.15 (s, 1H), 9.05 (d, 1H), 8.42 (dd, 1H), 8.29 (d, 1H), 7.88 (dt, 1H), 7.71 (t, 1H), 7.40 (m, 4H), 6.52 (d, 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-4f2f99b0414044acb08dcf623c9849d9 |
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| Source note | uspto-grants-2014_05 |
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