3-Aminopyridine → HCID 90040937, compound

Participants

Role	Name	HCID	Charge
Reactant	3-Aminopyridine	HCID 10009	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	2-Bromo-N-(1-hydroxy-2-methylpropan-2-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide	HCID 71575647	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane	HCID 31275	—
Solvent	Dichloromethane methanol	HCID 21226129	—
Product	HCID 90040937	HCID 90040937	18%

Reaction Conditions

Temperature	150 °C

Reaction Steps

A mixture of 2-bromo-N-(1-hydroxy-2-methylpropan-2-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (150 mg, 338 μmol), pyridin-3-amine (47.8 mg, 507 μmol), xantphos (58.7 mg, 101 μmol), Pd2(dba)3 (31.0 mg, 33.8 μmol) and cesium carbonate (220 mg, 677 μmol) 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, 40-100% ethyl acetate in hexanes gradient then dichloromethane/methanol) to give N-(1-hydroxy-2-methylpropan-2-yl)-2-(pyridin-3-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (32 mg, 59.6 μmol, 18%) as a light yellow solid. (EI/CI) m/z: 472.3 [M+H].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09334278B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-c92178c6981148998c343ad11a73c83c
Source note	uspto-grants-2016_05