Water → [2-Amino-6-[4,5-difluoro-2-(hydroxymethyl)phenyl]quinazolin-4-yl]isoindolin-2-ylmethanone

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	(2-Bromo-4,5-difluorophenyl)methanol	HCID 57518297	—
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	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Ethanol	HCID 702	—
Product	[2-Amino-6-[4,5-difluoro-2-(hydroxymethyl)phenyl]quinazolin-4-yl]isoindolin-2-ylmethanone	HCID 56943446	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

43 mg of (2-bromo-4,5-difluorophenyl)methanol, 80 mg of potassium carbonate, 4 μl of water and 16 mg of [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride are added to a solution of 100 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 10 ml of ethanol under argon. The mixture is heated at 120° C. for 30 min; during which a precipitate forms. After cooling to 22° C., 10 ml of water are added, and the precipitate is filtered off. The residue is washed 3 times with 25 ml of ethanol each time and dried at 40° C. in vacuo.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08791129B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-5c88f3c3e7ee4d59b76aa4a907b18448
Source note	uspto-grants-2014_07