Cesium carbonate → 5-(3,3-Dimethyl-but-1-ynyl)-3-[4-(pyridin-2-yloxy)-phenylamino]-thiophene-2-carboxylic acid methyl ester

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	2-(4-Bromophenoxy)pyridine	HCID 23201935	—
Edukt	Methyl 3-amino-5-(3,3-dimethylbut-1-yn-1-yl)thiophene-2-carboxylate	HCID 24989346	—
Katalysator	palladium(II) acetate	HCID 167845	—
Lösungsmittel	Toluene	HCID 1140	—
Lösungsmittel	Ethyl Acetate	HCID 8857	—
Produkt	5-(3,3-Dimethyl-but-1-ynyl)-3-[4-(pyridin-2-yloxy)-phenylamino]-thiophene-2-carboxylic acid methyl ester	HCID 58114098	66%

Reaktionsbedingungen

Temperatur	110 °C

Reaktionsschritte

A mixture of 3-amino-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester (0.200 g, 0.843 mmol), palladium acetate (0.019 g, 0.084 mmol), xantphos (0.058 g, 0.101 mmol), cesium carbonate (0.767 g, 2.36 mmol) and 2-(4-Bromo-phenoxy)-pyridine (0.252 g, 1.01 mmol) in toluene (3 mL) was heated by microwave to 110° C. for 45 minutes. The reaction was diluted with ethyl acetate filtered through a Celite pad and purified by silica gel chromatography to give 5-(3,3-Dimethyl-but-1-ynyl)-3-[4-(pyridin-2-yloxy)-phenylamino]-thiophene-2-carboxylic acid methyl ester in 66% yield.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US08569302B2
Quelldatensatz	uspto-grants-2013_10
ORD ID	ord-a428230856704956bebb63561fcaae31
Quellennotiz	uspto-grants-2013_10