2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → N-(2-Fluoro-4-(6-oxo-5,6-dihydrobenzo[c][1,8]naphthyridin-1-ylamino)phenyl) benzamide

Participants

Role	Name	HCID	Charge
Reactant	2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl	HCID 11155794	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	1-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one	HCID 58168008	—
Reactant	HCID 68648956	HCID 68648956	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	1,4-Dioxane	HCID 31275	—
Solvent	Water ethylacetate	HCID 22728543	—
Product	N-(2-Fluoro-4-(6-oxo-5,6-dihydrobenzo[c][1,8]naphthyridin-1-ylamino)phenyl) benzamide	HCID 44206392	54.2%

Reaction Conditions

Temperature	100 °C

Reaction Steps

The reaction mixture of 83 (80 mg, 0.35 mmol), N-(4-(4-amino-2-fluorophenyl amino)phenyl)benzamide (96 mg, 0.42 mmol), Pd(OAc)2 (12 mg, 0.05 mmol), X-Phos (50 mg, 0.10 mmol), and NaOtBu (67 mg, 0.69 mmol) in dioxane (2 mL) was stirred at 100° C. for 2 days. The reaction mixture was diluted with EtOAc/H2O. The resulting precipitate was filtered, washed with H2O, and dried under vacuum to provide 320 (23 mg, 16% yield) as a solid. LC-MS (M+H=425, obsd.=425).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08735584B2
Source dataset	uspto-grants-2014_05
ORD ID	ord-bc395ab7e77a4445915329c845280c9b
Source note	uspto-grants-2014_05