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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1487642Generated: October 31, 2026

Cesium carbonate → HCID 86726477, compound

https://huagongshe.com/reaction/1487642

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
ReactantBinap, (A+-)-HCID 634876—
Reactant6-(2-Chloro-4-(cyclopentyloxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbenzo[d]oxazoleHCID 86726420—
ReactantHCID 86726476HCID 86726476—
Catalystpalladium(II) acetateHCID 167845—
Solvent1,4-DioxaneHCID 31275—
ProductHCID 86726477HCID 8672647760%

Reaction Conditions

Temperature100 °C

Reaction Steps

To a degassed mixture of 6-(2-chloro-4-(cyclopentyloxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbenzo[d]oxazole (1 equiv), 5-chloro-1-(2-methoxyethyl)-1H-pyrazol-4-amine (1.5 equiv) and cesium carbonate (3 equiv) in 1,4-dioxane (0.06 M) was added palladium acetate (0.1 equiv) and 2,2′-bis-diphenylphosphanyl-[1,1′]binaphthalenyl (0.2 equiv). The reaction was stirred at 100° C. for 2 h. Upon completion, the reaction mixture was cooled to room temperature, and concentrated. The residue was purified by silica gel chromatography (1-2% MeOH in DCM) to afford the desired product (60% yield, crude) as a yellow solid which was used in next step without further purification. MS (ESI) m/z 638.2 [M+H]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09428509B2
Source datasetuspto-grants-2016_08
ORD IDord-ec62115b69064d76b8e9ecd59c31c6c6
Source noteuspto-grants-2016_08