Dicyclohexylamine → Ethyl 5-(3,3-dimethylbut-1-yn-1-yl)-4-methylisoxazole-3-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Dicyclohexylamine	HCID 7582	—
Reactant	3,3-Dimethyl-1-butyne	HCID 13512	—
Reactant	Ethyl 5-bromo-4-methyl-1,2-oxazole-3-carboxylate	HCID 58828802	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Acetonitrile	HCID 6342	—
Product	Ethyl 5-(3,3-dimethylbut-1-yn-1-yl)-4-methylisoxazole-3-carboxylate	HCID 118511143	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

Ethyl 5-bromo-4-methylisoxazole-3-carboxylate (Intermediate A) (100 mg, 0.427 mmol) and 3,3-dimethylbut-1-yne (0.058 mL, 0.470 mmol) in acetonitrile (3 mL) were degassed thoroughly refilling with nitrogen. Dicyclohexylamine (0.085 mL, 0.427 mmol), CuI (2.85 mg, 0.015 mmol) and PdCl2(PPh3)2 (7.50 mg, 10.68 mmol) were added. The mixture was stirred in the microwave at 100° C. for 45 mins. The resulting mixture was adsorbed onto silica and purification by chromatography eluting with 0-10% 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-5303c8d73467488787aa992bdcfd43de
Source note	uspto-grants-2016_08