Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 3-Chlorophenol | HCID 7933 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 58168117 | HCID 58168117 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58168186 | HCID 58168186 | 83% |
Reaction Steps
9-Fluoro-5H-benzo[c][1,8]naphthyridin-6-one (40 mg, 0.19 mmol), 3-chlorophenol (72 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 73 (50 mg, 83% yield) as a tan solid. LC-MS (M+H=323, obsd.=323). 1H NMR (400 MHz, d6-DMSO): δ 12.05 (s, 1H), 8.78 (dd, 1H), 8.51 (dd, 1H), 8.35 (d, 1H), 8.19 (d, 1H), 7.49 (t, 1H), 7.29 (m, 4H), 7.12 (dd, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08735584B2 |
|---|
| Source dataset | uspto-grants-2014_05 |
|---|
| ORD ID | ord-895854ec5ff44da28bb45fd29c8e6d1e |
|---|
| Source note | uspto-grants-2014_05 |
|---|