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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 872320Generated: October 31, 2026

Sodium Carbonate → HCID 178452596, compound

https://huagongshe.com/reaction/872320

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
ReactantAmmonium ChlorideHCID 25517—
Reactant1H-Pyrazole-5-boronic acid, N1-BOC protectedHCID 46738924—
Reactant{1-[4-(7-Bromo-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterHCID 66665545—
SolventWaterHCID 962—
SolventDichloromethaneHCID 6344—
Solvent1,4-DioxaneHCID 31275—
ProductHCID 178452596HCID 178452596—

Reaction Conditions

Temperature105 °C

Reaction Steps

To a solution of {1-[4-(7-bromo-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (200 mg, 0.38 mmol), and 1-(tert-butoxycarbonyl)pyrazole-5-boronic acid (164 mg, 0.77 mmol, 2 equiv) in dioxane (4 mL) under argon was added [1,1-bis(diphenylphosphino)ferrocene]dichloro-palladium(II) CH2Cl2 complex (63 mg, 0.77 mmol, 20 mol %), Na2CO3 (123 mg, 1.16 mmol, 3 equiv) and water (0.5 mL). The resulting mixture was heated at 105° C. for 8 h in a microwave apparatus. The reaction mixture was mixed with water (10 mL), a saturated aqueous NH4Cl solution (10 mL) and CH2Cl2 (25 mL) with vigorous stirring at room temperature for 30 min. The organic phase was washed with a saturated aqueous NaCl solution (25 mL), dried (Na2SO4 anh), and concentrated under reduced pressure.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08975265B2
Source datasetuspto-grants-2015_03
ORD IDord-9333544ff08c4662b0e2f8f035742928
Source noteuspto-grants-2015_03