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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1029102Generated: October 31, 2026

P-Anisidine → HCID 58167987, compound

https://huagongshe.com/reaction/1029102

Reaction equation

Participants

RoleNameHCIDCharge
ReactantP-AnisidineHCID 7732—
Reactant2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 11155794—
ReactantSodium t-butoxideHCID 23676156—
ReactantHCID 58167982HCID 58167982—
Catalystpalladium(II) acetateHCID 167845—
SolventMethanolHCID 887—
Solvent1,4-DioxaneHCID 31275—
ProductHCID 58167987HCID 5816798738.2%

Reaction Conditions

Temperature100 °C

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08735584B2
Source datasetuspto-grants-2014_05
ORD IDord-f1b0a8df602b43bc810a3235136a8f29
Source noteuspto-grants-2014_05