Diisopropylethylamine → HCID 66765112, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Isooctyl 3-mercaptopropionate	HCID 104386	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	Ethyl 3-bromo-4-methoxybenzoate	HCID 23062539	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 66765112	HCID 66765112	—

Reaction Conditions

Temperature	90 °C

Reaction Steps

3-Bromo-4-methoxy-benzoic acid ethyl ester (1.61 g, 6.62 mmol) and isooctyl-3-mercaptopropionate (1.73 g, 7.95 mmol) were dissolved in dioxane (26 mL) and the mixture was sparged with N2 (g) for 10 minutes. Diisopropylethyl amine (2.31 mL, 13.25 mmol), Xanthphos (0.1917 g, 0.33 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.1517 g, 0.166 mmol) were added and the mixture was sparged with N2 (g) for 5 minutes. The reaction was then heated to 90° C. for 2 hours after which time it was filtered to remove solid impurities. The mixture was concentrated and the residue was purified on silica gel (0-40% EtOAc in hexanes) to give the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09000025B2
Source dataset	uspto-grants-2015_04
ORD ID	ord-ec88ccc5db564be69341524009f9268d
Source note	uspto-grants-2015_04