Triethylamine → Tert-butyl 4-[6-[6-(6-vinylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperazine-1-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Potassium vinyltrifluoroborate	HCID 23679353	—
Reactant	tert-butyl 4-(6-(6-(6-chloropyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperazine-1-carboxylate	HCID 86707183	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Ethanol	HCID 702	—
Product	Tert-butyl 4-[6-[6-(6-vinylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperazine-1-carboxylate	HCID 86707182	—

Reaction Conditions

Temperature	105 °C

Reaction Steps

A mixture of tert-butyl 4-[6-[6-(6-chloropyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperazine-1-carboxylate (493 mg, 1 mmol), potassium vinyltrifluoroborate (335 mg, 2.500 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride, DCM complex (55 mg, 0.07500 mmol) and triethylamine (0.63 ml, 4.500 mmol) in ethanol (9 mL) was degassed and heated in a sealed vial for 2 hours at 105° C. The mixture was left at room temperature for 20 hours. The precipitate was collected and washed with ethanol to give the crude material, 605 mg (99.8%). MS (ESI) m/z: 485.4 [M+H]+

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09434725B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-451dddd0ce244ba4bc8f82f9a69a950e
Source note	uspto-grants-2016_09