Water → 2-[2-Amino-4-(isoindoline-2-carbonyl)quinazolin-6-yl]-5-hydroxybenzaldehyde

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2-Bromo-5-hydroxybenzaldehyde	HCID 387179	—
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-[2-Amino-4-(isoindoline-2-carbonyl)quinazolin-6-yl]-5-hydroxybenzaldehyde	HCID 86689439	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

72 mg of 2-bromo-5-hydroxybenzaldehyde, 100 mg of potassium carbonate, 1 ml of water and 15 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 3 ml of ethanol under argon. The mixture is heated at 120° C. for min; the hot mixture is filtered through kieselguhr, and the filtrate is evaporated. The residue obtained was triturated with 2 ml of acetonitrile, and the precipitate formed was filtered off with suction. Yield: 56 mg (38%) of 2-[2-amino-4-(isoindoline-2-carbonyl)quinazolin-6-yl]-5-hydroxybenzaldehyde; HPLC retention time: 1.67 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08791129B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-6fafe939b0e0482d9358ac54d3df9a6c
Source note	uspto-grants-2014_07