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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 921798Generated: October 30, 2026

Cesium carbonate → HCID 86708696, compound

https://huagongshe.com/reaction/921798

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
Reactant1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 636044—
Reactant2-Chloro-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrileHCID 86708477—
ReactantHCID 86708695HCID 86708695—
Catalystpalladium(II) acetateHCID 167845—
CatalystFerrocene-1,1'-bis-(diphenylphosphine)HCID 635956—
Solvent1,4-DioxaneHCID 31275—
ProductHCID 86708696HCID 8670869640.8%

Reaction Conditions

Temperature80 °C

Reaction Steps

A mixture of 2-chloro-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (Intermediate 9) (47.4 mg, 0.134 mmol), 3-amino-4-chloro-5-((1-(3-methyloxetan-3-yl)piperidin-4-yl)oxy)benzonitrile (43 mg, 0.134 mmol), palladium(II) acetate (7.95 mg, 0.035 mmol), xantphos (7.73 mg, 0.013 mmol), DPPF (7.41 mg, 0.013 mmol) and cesium carbonate (113 mg, 0.347 mmol) in dioxane (2 ml) was evacuated and back filled with nitrogen three time and was heated at 80° C. for 6 h. The reaction mixture was filtered through a pad of celite, the filtrate was concentrated and the crude was purified by prep-HPLC. 2-((2-chloro-5-cyano-3-((1-(3-methyloxetan-3-yl)piperidin-4-yl)oxy)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (35 mg) was obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09273057B2
Source datasetuspto-grants-2016_03
ORD IDord-014cb35f233649fca1b2f77d94852803
Source noteuspto-grants-2016_03