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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1622374Generated: October 31, 2026

Sodium Carbonate → HCID 45275574, compound

https://huagongshe.com/reaction/1622374

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant3,5-Dimethylisoxazole-4-boronic acidHCID 2734346—
ReactantHCID 45275354HCID 45275354—
CatalystHCID 178418397HCID 178418397—
SolventAcetonitrileHCID 6342—
ProductHCID 45275574HCID 4527557417%

Reaction Steps

General procedure E was followed using 1-(3-bromopyridin-4-yl)piperidine-4-carboxamide E36 (100 mg, 0.35 mmol), 3,5-dimethyl-4-isoxazole boronic acid (74 mg, 0.53 mmol), tetrakis(triphenylphosphine)palladium(0) (20 mg, 5 mol %), acetonitrile (4 mL) and 0.5 M sodium carbonate (1.1 mL, 0.53 mmol). The crude product was purified by flash column chromatography on silica gel (CH2Cl2, EtOH, 97:3-80:20, biotage 25+S) to furnish the title compound as a white solid (18 mg, 17%), along with 1-(3-bromopyridin-4-yl)piperidine-4-carboxamide (10 mg, 10% RSM), LC-MS (ESI, 4 min) Rt 0.76 min, m/z 301 (100%, [M+H]+); m/z (ESI, Rt 1.22 min) C16H20N4O2 requires 300.1587, found [M+H]+ 300.1591.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08778925B2
Source datasetuspto-grants-2014_07
ORD IDord-9d1c373d88a44d3f987bc89403f69313
Source noteuspto-grants-2014_07