Water → [2-(2-Bromo-4,5-difluorobenzyloxy)ethyl]dimethylamine

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	[2-Amino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-4-yl]-(1,3-dihydroisoindol-2-yl)methanone	HCID 58457219	—
Reactant	[3-(2-Bromo-4,5-difluorobenzyloxy)propyl]dimethylamine	HCID 66836744	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Ethanol	HCID 702	—
Product	[2-(2-Bromo-4,5-difluorobenzyloxy)ethyl]dimethylamine	HCID 66836629	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

88 mg of [3-(2-bromo-4,5-difluorobenzyloxy)propyl]dimethylamine, 80 mg of potassium carbonate, 5 μl of water and 12 mg of [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride are added to a solution of 150 mg of [2-amino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-4-yl]-(1,3-dihydroisoindol-2-yl)methanone in 2 ml of ethanol under argon. The mixture is heated at 120° C. for 60 min. The solid is subsequently filtered off through kieselguhr with suction, and the filtrate is evaporated to dryness in vacuo. The residue is dissolved in 1 ml of DMSO and chromatographed by means of preparative HPLC (Agilent). The product fractions obtained are subsequently evaporated and freeze-dried.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08791129B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-5e68aaf9068c484498d6a0125a443f18
Source note	uspto-grants-2014_07