Diisopropylethylamine → tert-butyl 3-(2-neopentyl-1-(2-(trifluoromethoxy)ethyl)-1H-benzo[d]imidazol-5-ylthio)azetidine-1-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	tert-Butyl 3-sulfanylazetidine-1-carboxylate	HCID 58513580	—
Reactant	5-bromo-2-neopentyl-1-(2-(trifluoromethoxy)ethyl)-1H-benzo[d]imidazole	HCID 58513596	—
Catalyst	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	tert-butyl 3-(2-neopentyl-1-(2-(trifluoromethoxy)ethyl)-1H-benzo[d]imidazol-5-ylthio)azetidine-1-carboxylate	HCID 58513590	81.5%

Reaction Conditions

Temperature	160 °C

Reaction Steps

A mixture of 5-bromo-2-neopentyl-1-(2-(trifluoromethoxy)ethyl)-1H-benzo[d]imidazole (STEP A, 265 mg, 0.700 mmol), tert-butyl 3-mercaptoazetidine-1-carboxylate (STEP D of Example 1, 189 mg, 0.999 mmol), Xantphos (20.2 mg, 0.0350 mmol), tris(dibenzylideneacetone)dipalladium (16.0 mg, 0.0175 mmol) and N,N-diisopropylethylamine (245 microL, 1.40 mmol) in 1,4-dioxane (4 mL) was stirred at 160° C. for 1 h under microwave. The mixture was diluted with ethyl acetate and filtered through a celite. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (hexane-ethyl acetate, gradient) to give the title compound (278 mg, 81%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08653063B2
Source dataset	uspto-grants-2014_02
ORD ID	ord-551daae415654aa68146d63cf51636aa
Source note	uspto-grants-2014_02