Cesium carbonate → N-tert-butyl-2-(methyl(pyridin-3-yl)amino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

https://huagongshe.com/de/reaction/522986

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Cesium carbonate	HCID 10796	—
Edukt	N-Methyl-3-pyridinamine	HCID 140376	—
Edukt	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Edukt	2-bromo-N-(tert-butyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide	HCID 71575645	—
Katalysator	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Lösungsmittel	1,4-Dioxane	HCID 31275	—
Produkt	N-tert-butyl-2-(methyl(pyridin-3-yl)amino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide	HCID 90041212	29%

Reaktionsbedingungen

Temperatur	150 °C

Reaktionsschritte

A mixture of 2-bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (125 mg, 292 μmol), N-methylpyridin-3-amine (47.4 mg, 439 μmol), xantphos (50.8 mg, 87.7 μmol), Pd2(dba)3 (26.8 mg, 29.2 μmol) and cesium carbonate (191 mg, 585 μmol) in dioxane (2 mL) was heated in a microwave at 150° C. for 20 min. The mixture was cooled and then filtered through a pad of celite. The filtrate was concentrated in vacuo then purified by chromatography (silica, ethyl acetate in hexanes) to give N-tert-butyl-2-(methyl(pyridin-3-yl)amino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (38 mg, 83.6 μmol, 29%) as a yellow gum. (EI/CI) m/z: 455.4 [M+H].

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US09334278B2
Quelldatensatz	uspto-grants-2016_05
ORD ID	ord-79dc9df8e7b743ae89ee0b36e29d3630
Quellennotiz	uspto-grants-2016_05