Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 4-Chlorophenol | HCID 4684 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 58168117 | HCID 58168117 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58168060 | HCID 58168060 | 98% |
Reaction Steps
9-Fluoro-5H-benzo[c][1,8]naphthyridin-6-one (40 mg, 0.19 mmol), 4-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 74 (59 mg, 98% yield) as a tan solid. LC-MS (M+H=323, obsd.=323). 1H NMR (400 MHz, d6-DMSO): δ 12.02 (s, 1H), 8.77 (dd, 1H), 8.51 (dd, 1H), 8.33 (d, 1H), 8.15 (d, 1H), 7.52 (m, 2H), 7.23 (m, 4H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08735584B2 |
|---|
| Source dataset | uspto-grants-2014_05 |
|---|
| ORD ID | ord-6e2e5bc528da4745b2d419c1acd331e3 |
|---|
| Source note | uspto-grants-2014_05 |
|---|