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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 535414Generated: November 3, 2026

Sodium Carbonate → HCID 86694401, compound

https://huagongshe.com/reaction/535414

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant1,4-DioxaneHCID 31275—
ReactantQuinoline-3-boronic acidHCID 2734663—
ReactantHCID 86694402HCID 86694402—
CatalystHCID 178418476HCID 178418476—
SolventMethanolHCID 887—
SolventWaterHCID 962—
SolventDichloromethaneHCID 6344—
ProductHCID 86694401HCID 86694401—

Reaction Conditions

Temperature85 °C

Reaction Steps

A mixture of tert-butyl-N-[1-[[5-bromo-6-(2-naphthalen-2-ylethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]-N-methylcarbamate C2c (150 mg, 0.30 mmol), quinolin-3-ylboronic acid (61 mg, 0.35 mmol), Dichlorobis(triphenylphosphine)palladium(II) (40 mg, 0.06 mmol), Na2CO3 (63 mg, 0.59 mmol), dioxane (1 ml), MeOH (0.2 ml) and water (0.1 ml) is stirred under argon atmosphere for 2 h at 85° C. The mixture is diluted with DCM and extracted with a saturated aqueous solution of NaHCO3. The combined organic layers are dried over MgSO4, concentrated in vacuo and the product purified by RP HPLC. Yield: 91 mg (55%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08859541B2
Source datasetuspto-grants-2014_10
ORD IDord-1351bc3bbae344c9bcb393bfac87f6f5
Source noteuspto-grants-2014_10