Cyclohexanone → Ethyl 1-(3-(naphthalen-1-yloxy)propyl)-4-(2-oxocyclohexyl)-1h-indole-2-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Cyclohexanone	HCID 7967	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	HCID 67316436	HCID 67316436	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Water	HCID 962	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	Ethyl 1-(3-(naphthalen-1-yloxy)propyl)-4-(2-oxocyclohexyl)-1h-indole-2-carboxylate	HCID 67315704	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

To a solution of EXAMPLE 106B (438 mg) and cyclohexanone (196 mg) in dioxane (3 ml) was added tris(dibenzylideneacetone)dipalladium(0) (5 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos, 7 mg) and Cs2CO3 (652 mg). The mixture was stirred at 80° C. under nitrogen overnight. After cooling, the reaction mixture was diluted with ethyl acetate and shaken with water. The product was extracted with ether (200 ml×3). The combined organic extracts were washed with water, brine, and dried over Na2SO4. After filtration, concentration of the mixture and flash column purification (3% ethyl acetate in hexane) provided EXAMPLE 106C.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08853209B2
Source dataset	uspto-grants-2014_10
ORD ID	ord-71249f500298463da5c2b1c6c39cc121
Source note	uspto-grants-2014_10