2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → 1-(5-Chloro-benzo[1,3]dioxol-4-ylamino)-5H-benzo[c][1,8]naphthyridin-6-one

Participants

Role	Name	HCID	Charge
Reactant	2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl	HCID 11155794	—
Reactant	5-Chloro-1,3-benzodioxol-4-amine	HCID 11367253	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	1-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one	HCID 58168008	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	1,4-Dioxane	HCID 31275	—
Solvent	Water ethylacetate	HCID 22728543	—
Product	1-(5-Chloro-benzo[1,3]dioxol-4-ylamino)-5H-benzo[c][1,8]naphthyridin-6-one	HCID 58168300	76.2%

Reaction Conditions

Temperature	100 °C

Reaction Steps

Compound 83 (250 mg, 1.08 mmol), 5-chloro-benzo[1,3]dioxol-4-ylamine (279 mg, 1.63 mmol), Pd(OAc)2 (12 mg, 0.05 mmol), X-Phos (52 mg, 0.11 mmol), and NaOtBu (312 mg, 3.25 mmol) were suspended in dioxane (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 188 (301 mg, 76% yield) as a white solid. LC-MS (M+H=366, obsd.=366).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08735584B2
Source dataset	uspto-grants-2014_05
ORD ID	ord-ff3094e82c84411fac9cd09cd3477029
Source note	uspto-grants-2014_05