Cesium carbonate → HCID 90041584, compound

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	5-Amino-3-methylisoxazole	HCID 84590	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	2-bromo-N-(tert-butyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide	HCID 71575645	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 90041584	HCID 90041584	25.4%

Reaction Conditions

Temperature	150 °C

Reaction Steps

A mixture of 2-bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (125 mg, 292 mol), 3-methylisoxazol-5-amine (43.0 mg, 439 mol), xantphos (50.8 mg, 87.7 mol), Pd2(dba)3 (26.8 mg, 29.2 mol) and cesium carbonate (191 mg, 585 mol) in dioxane (2 mL) was heated in a microwave at 150° C. for 20 min. The mixture was cooled then filtered through a pad of celite. The filtrate was concentrated in vacuo then purified by chromatography (silica, 20-75% ethyl acetate in hexanes) to give N-tert-butyl-2-(3-methylisoxazol-5-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (33 mg, 74.2 mol, 25.4%) as a yellow solid. (EI/CI) m/z: 455.3 [M+H].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09334278B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-290fca5da42143bea555ac48637dfe96
Source note	uspto-grants-2016_05