Dichloromethane → Ethyl 4-methyl-5-(2-oxaspiro[4.5]dec-7-en-8-yl)isoxazole-3-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Ethyl 5-bromo-4-methyl-1,2-oxazole-3-carboxylate	HCID 58828802	—
Reactant	4,4,5,5-Tetramethyl-2-(2-oxaspiro[4.5]dec-7-en-8-yl)-1,3,2-dioxaborolane	HCID 131289331	—
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	—
Product	Ethyl 4-methyl-5-(2-oxaspiro[4.5]dec-7-en-8-yl)isoxazole-3-carboxylate	HCID 118511182	—

Reaction Conditions

Temperature	90 °C

Reaction Steps

[4,4,5,5-tetramethyl-2-(2-oxaspiro[4.5]dec-7-en-8-yl)-1,3,2-dioxaborolane] (0.172 g, 0.651 mmol), ethyl 5-bromo-4-methylisoxazole-3-carboxylate (Intermediate A) (0.183 g, 0.781 mmol) and Cs2CO3 (0.849 g, 2.60 mmol) were combined in DME (3 mL) and water (1.250 mL). PdCl2(dppf).CH2Cl2 adduct (0.016 g, 0.020 mmol) was added and the mixture was degassed thoroughly refilling with nitrogen. The mixture was stirred in the microwave at 90° C. for 1 hour. The biphasic reaction mixture was separated and the organic phase was adsorbed onto silica. Purification by chromatography eluting with a gradient of EtOAc in iso-hexane afforded the title compound;

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09403810B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-8ce6b326991b49dabf6ad5e0c9a70a2f
Source note	uspto-grants-2016_08