Cesium carbonate → (3aR,6aR)-tert-butyl 1-(5-(3,5-difluorophenylcarbamoyl)pyridin-3-yl)hexahydropyrrolo[3,2-c]pyrrole-5(1H)-carboxylate

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Cesium carbonate	HCID 10796	—
Edukt	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Edukt	tert-butyl (3aR,6aR)-2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[2,3-c]pyrrole-5-carboxylate	HCID 37818785	—
Edukt	5-bromo-N-(3,5-difluorophenyl)nicotinamide	HCID 41601149	—
Katalysator	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Lösungsmittel	1,4-Dioxane	HCID 31275	—
Produkt	(3aR,6aR)-tert-butyl 1-(5-(3,5-difluorophenylcarbamoyl)pyridin-3-yl)hexahydropyrrolo[3,2-c]pyrrole-5(1H)-carboxylate	HCID 67265787	—

Reaktionsschritte

A suspension of (3aR,6aR)-tert-butyl hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate (85 mg, 0.40 mmol, prepared as described in WO2001081347), the product from Example 53A (97 mg, 0.37 mmol), tris(dibenzylideneacetone)dipalladium(0) (13.4 mg, 0.015 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (25 mg, 0.044 mmol) and cesium carbonate (190 mg, 0.58 mmol) in anhydrous dioxane (4 mL) was heated at 90° C. for 18 hours. The reaction mixture was cooled and filtered through a glass frit. The filtrate was concentrated and the residue was purified by silica gel chromatography (EtOAc, Rf=0.4) to afford the title compound. MS (APCI) m/z=445 (M+H)+.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US08648084B2
Quelldatensatz	uspto-grants-2014_02
ORD ID	ord-164d96d3bf3f4625ba5fcad317a66c98
Quellennotiz	uspto-grants-2014_02