Potassium Phosphate, Tribasic → 4-{4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-naphthalen-1-yl}-pyrazole-1-carboxylic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate	HCID 16217654	—
Reactant	3-(4-Bromo-1-naphthalenyl)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)isoxazole	HCID 86645277	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Toluene	HCID 1140	—
Product	4-{4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-naphthalen-1-yl}-pyrazole-1-carboxylic acid tert-butyl ester	HCID 67436208	—

Reaction Conditions

Temperature	75 °C

Reaction Steps

1-Tert-butoxycarbonyl-4-1H-pyrazoleboronic acid pinacol ester (126 mg), Tris(dibenzylideneacetone)dipalladium(0) [Pd2(dba)3 (7 mg)], K3PO4 (185 mg) and 2-dicyclohexylphosphinno-2′,6′-dimethoxybiphenyl (12 mg) are added to a solution of 3-(4-bromo-naphthalen-1-yl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole (140 mg) in dry toluene (2.4 ml). After 16 hours at 75° C. the reaction is cooled down to room temperature and filtrated. The filtrate is concentrated in vacuo. The crude product is purified on a semi-preparative HPLC to yield 4-{4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-naphthalen-1-yl}-pyrazole-1-carboxylic acid tert-butyl ester (compound 1.10, Table 1) as a colorless oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08377942B2
Source dataset	uspto-grants-2013_02
ORD ID	ord-943387d0212c431fa87db4d94dfbf64d
Source note	uspto-grants-2013_02