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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 733Erstellt: 23. Oktober 2026

6-Hydroxymethylindole → 7-(Cyclopropylamino)-5-[6-(hydroxymethyl)indol-1-yl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile

https://huagongshe.com/de/reaction/733

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
Edukt6-HydroxymethylindoleHCID 2773459—
Edukt5-Chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrileHCID 89827173—
ReagenzCesium carbonateHCID 10796—
Katalysator1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 636044—
KatalysatorBis(dibenzylideneacetone)palladiumHCID 9811564—
LösungsmittelDimethylacetamideHCID 31374—
Produkt7-(Cyclopropylamino)-5-[6-(hydroxymethyl)indol-1-yl]pyrazolo[1,5-a]pyrimidine-3-carbonitrileHCID 7069277547,5%

Reaktionsbedingungen

Temperatur150 °C

Reaktionsschritte

In a 40mL vial (t=g) was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (50 mg, 0.21 mmol), [Reactants], and cesium carbonate (77 mg, 0.24 mmol) in DMA (0.5 mL) ([VOLUME]),Pd2(dba)3 (9.80 mg, 10.70 µmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (12.38 mg, 0.02 mmol) were added. to give a brown suspension. The vial was filled with N2, 150C microwave for 30 min. LCMS showed completion. added MeOH (3 mL), filtered through celite. concentrated. The residue was purified by ISCO (Hexane to EtOAc:Hex=1;1 to EtOAc) to give about 34 mg offwhite solid

Herkunft & Nachweise

Quelldatensatz750 AstraZeneca ELN dataset
ORD IDord-e0d4157f08c0492097a16f50798a4aa4
Quellennotiz750 AstraZeneca ELN dataset