Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | P-Anisidine | HCID 7732 | — |
| Reactant | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | HCID 58167982 | HCID 58167982 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 58167987 | HCID 58167987 | 38.2% |
Reaction Steps
2-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (30 mg, 0.13 mmol), 4-methoxy aniline (32 mg, 0.26 mmol), palladium(II) acetate (2 mg, 0.01 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (6 mg, 0.02 mmol), and sodium tert-butoxide (38 mg, 0.39 mmol) were suspended in dioxane (2 mL), and stirred overnight at 100° C. The reaction mixture was diluted with MeOH, filtered, and purified via prep-LC-MS to provide 87 (15 mg, 36% yield) as a solid. LC-MS (M+H=318, obsd.=318). 1H NMR (400 MHz, d6-DMSO): δ 11.86 (s, 1H), 8.33 (dd, 2H), 8.22 (m, 2H), 7.88 (dt, 1H), 7.68 (m, 1H), 7.11 (d, 2H), 6.91 (d, 2H), 3.73 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08735584B2 |
|---|
| Source dataset | uspto-grants-2014_05 |
|---|
| ORD ID | ord-f1b0a8df602b43bc810a3235136a8f29 |
|---|
| Source note | uspto-grants-2014_05 |
|---|