Water → 3-(Oxetan-2-ylmethoxy)-5-(4-(trifluoromethoxy)phenyl)benzo[d]isoxazole

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	4-(Trifluoromethoxy)phenylboronic acid	HCID 2734386	—
Reactant	5-Bromo-3-(pyrimidin-2-ylmethoxy)benzo[d]isoxazole	HCID 118161969	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	3-(Oxetan-2-ylmethoxy)-5-(4-(trifluoromethoxy)phenyl)benzo[d]isoxazole	HCID 118161912	—

Reaction Conditions

Temperature	60 °C

Reaction Steps

5-Bromo-3-(pyrimidin-2-ylmethoxy)benzo[d]isoxazole (114 mg, 0.40 mmol), 4-(trifluoromethoxy)phenylboronic acid (100 mg, 0.49 mmol), potassium carbonate (500 mg), and [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (25 mg, 0.034 mmol) were combined in 3 mL DMF. 1.5 mL water was added and the mixture was stirred at 60° C. for 30 minutes. The reaction mixture was diluted with 60 mL ethyl acetate, washed with water and brine and evaporated under vacuum. Flash chromatographic purification on 12 g silica gel with 0-60% ethyl acetate in hexane gave the title compound (115 mg, 0.31 mmol).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09416115B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-b9760a04e7f54eab9dbf7f444b895807
Source note	uspto-grants-2016_08