Potassium Hydroxide → HCID 58168126, compound

Participants

Role	Name	HCID	Charge
Reactant	Potassium Hydroxide	HCID 14797	—
Reactant	2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl	HCID 11155794	—
Reactant	1-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one	HCID 58168008	—
Reactant	HCID 68648690	HCID 68648690	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	2-Methyl-2-butanol	HCID 6405	—
Solvent	Water ethylacetate	HCID 22728543	—
Product	HCID 58168126	HCID 58168126	28.2%

Reaction Conditions

Temperature	100 °C

Reaction Steps

Compound 83 (100 mg, 0.43 mmol), 1-(4-isopropyl-phenyl)-3-piperidin-4-yl-urea (136 mg, 0.52 mmol), Pd(OAc)2 (5 mg, 0.02 mmol), X-Phos (21 mg, 0.04 mmol), and KOH (73 mg, 1.30 mmol) were suspended in tert-amyl alcohol (2 mL), and stirred overnight at 100° C. The reaction mixture was diluted with EtOAc/H2O. The resulting precipitate was filtered, washed with EtOAc/H2O, and dried under vacuum to provide 159 (40 mg, 28% yield) as a tan solid. LC-MS (M+H=330, obsd.=330).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08735584B2
Source dataset	uspto-grants-2014_05
ORD ID	ord-bbf04dd138ef41cb87a0357aa2ad6e27
Source note	uspto-grants-2014_05