Dichloromethane → 5-(4-(4-(6-Methylpyridin-3-yloxy)-3-methylphenylamino)quinazolin-6-yl)furan-2-carbaldehyde

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	1,2-Dimethoxyethane	HCID 8071	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	(6-Iodo-quinazolin-4-yl)-[3-methyl-4-(6-methyl-pyridin-3-yloxy)-phenyl]-amine	HCID 11282772	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Ethanol	HCID 702	—
Product	5-(4-(4-(6-Methylpyridin-3-yloxy)-3-methylphenylamino)quinazolin-6-yl)furan-2-carbaldehyde	HCID 86668477	98%

Reaction Conditions

Temperature	75 °C

Reaction Steps

Under nitrogen atmosphere, Pd(dppf)2Cl2 (85 mg) was added to a mixture of N-(4-(6-methylpyridin-3-yloxy)-3-methylphenyl)-6-iodoquinazolin-4-amine (468 mg, 1 mmole), 5-formylfuran-2-yl-2-boronic acid (170 mg) and 2M K2CO3 (4 mL) in Ethanol (4 mL) and DME (4 mL). The reaction mixture was heated at 75° C. for 4 h and cooled down to room temperature. Methylene chloride (30 mL) was added and washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography, eluting with 20% methanol in dichloromethane to give the desired product as white solid (430 mg). LCMS ESI(+) m/z: 437 (M+1). Yield: 98%.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08987284B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-50713bc4d77344d6bf31dda6007e9482
Source note	uspto-grants-2015_03