Potassium Carbonate → HCID 117601838, compound

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	4-Bromo-2-nitroaniline	HCID 70132	—
Reactant	3,5-Dimethylisoxazole-4-boronic acid pinacol ester	HCID 2758656	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 117601838	HCID 117601838	93.1%

Reaction Conditions

Temperature	95 °C

Reaction Steps

To a mixture of 4-bromo-2-nitro-phenylamine (150 g, 0.691 mol, 1.0 eq) and 3,5-dimethylisoxazole-4-boronic acid pinacol ester (169 g, 0.725 mol, 1.05 eq) in 1,2-dimethoxyethane (1.5 L) and water (700 mL) were added PdCl2(dppf) (56 g, 69 mmol, 0.1 eq) and K2CO3 (190 g, 1.38 mol, 2.0 eq). The reaction mixture was heated at 95° C. overnight. The reaction mixture was diluted with EtOAc (3 L), washed with brine (2×500 mL). The organic solvent was evaporated and the residue was purified with flash chromatography on silica (PE/EA=10:1-1:1) to give 150 g 4-(3,5-dimethylisoxazol-4-yl)-2-nitroaniline as a red solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09255089B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-9ad5b9dbc33746abadb61b8273aa92e7
Source note	uspto-grants-2016_02