Sodium Carbonate → 5-(3,5-Dimethylisoxazol-4-yl)-3-hydroxy-3-phenylindolin-2-one

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	Lithium Chloride	HCID 433294	—
Reactant	3,5-Dimethylisoxazole-4-boronic acid	HCID 2734346	—
Reactant	3-Hydroxy-5-iodo-3-phenyl-1,3-dihydro-indol-2-one	HCID 117599670	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane--water (1/1)	HCID 21886435	—
Product	5-(3,5-Dimethylisoxazol-4-yl)-3-hydroxy-3-phenylindolin-2-one	HCID 86296101	—

Reaction Conditions

Temperature	130 °C

Reaction Steps

3-Hydroxy-5-iodo-3-phenyl-1,3-dihydro-indol-2-one (130 mg, 0.370 mmol), 3,5-dimethyl-4-isoxazolylboronic acid (104 mg, 0.740 mmol), sodium carbonate (108 mg, 1.025 mmol), Pd(dppf)Cl2 (57 mg, 78 mmol) and lithium chloride (114.5 mg, 2.700 mmol) are added to a microwave vial. Dioxane/water (2:1, 3 mL) is added. The mixture is flushed with argon and the vessel heated at 130° C. for 1 h. The reaction mixture is diluted with water and dcm then extracted with dcm. The organic layer is dried with Na2SO4, filtered and concentrated under reduced pressure. The residue is dissolved in DMSO, filtered and purified with the acidic (formic acid) RP HPLC system. The product containing fractions are concentrated under reduced pressure. Dissolved in DMSO, aliquoted and freeze dried. Once more freeze dried with acetonitril: water. This afforded the desired product.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09102684B2
Source dataset	uspto-grants-2015_08
ORD ID	ord-e0c27a533b9e4684aacc8378723e8865
Source note	uspto-grants-2015_08