Cesium carbonate → HCID 131735560, compound

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	tert-Butyl [1-(3-aminophenyl)ethyl]carbamate	HCID 16740730	—
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 131735560	HCID 131735560	73.2%

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 (150 mg, 351 mol), tert-butyl 1-(3-aminophenyl)ethylcarbamate (124 mg, 526 mol), xantphos (60.9 mg, 105 mol), Pd2(dba)3 (32.1 mg, 35.1 mol) and cesium carbonate (229 mg, 702 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, 20-40% ethyl acetate in hexanes) gave tert-butyl 1-(3-(7-(tert-butylcarbamoyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)phenyl)ethylcarbamate (150 mg, 257 mol, 73%) as a yellow gum. (EI/CI) m/z: 583.5 [M+H].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09334278B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-0c7f044821c4472ca9a4ece043ac5da2
Source note	uspto-grants-2016_05