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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2209162Generated: October 30, 2026

Sodium Carbonate → HCID 117843014, compound

https://huagongshe.com/reaction/2209162

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant(R)-4-((R)-1-((6-bromo-3-cyclopropyl-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-onHCID 117843105—
ReactantHCID 123306863HCID 123306863—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
Solvent1,4-DioxaneHCID 31275—
ProductHCID 117843014HCID 1178430143.6%

Reaction Steps

To a 2-5 ml microwave vial, combined (R)-4-((R)-1-((6-bromo-3-cyclopropyl-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one (85 mg, 0.23 mmol), 4-(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)azetidin-3-yl)morpholine (100.15 mg, 0.29 mmol), tetrakis(triphenylphosphine)palladium (26.89 mg, 0.02 mmol), 1M Sodium carbonate soln in water (0.7 ml) in dioxane (2.3 mL) and blown down with nitrogen. The reaction was irradiated for 20 mins at 150 C. The reaction was diluted with water, extracted with DCM, combined organics, dried (Na2SO4), filtered, concentrated. Residues were purified by silica gel column chromatography to yield the title compound (4.2 mg, 3.6%) as a free base.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09376441B2
Source datasetuspto-grants-2016_06
ORD IDord-25a170855cc849b2b3432e18c5e1785c
Source noteuspto-grants-2016_06