6-Hydroxymethylindole → HCID 70692775, Verbindung

HRID 733

Reaktionsgleichung

Reaktionsgleichung von HRID 733
N#Cc1cnn2c(NC3CC3)cc(Cl)nc12.OCc1ccc2cc[nH]c2c1>CC(=O)N(C)C.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].[Pd]>N#Cc1cnn2c(NC3CC3)cc(-n3ccc4ccc(CO)cc43)nc12

Komponenten

7

Edukt 2

HCID 27734596-HydroxymethylindoleHCID 898271735-Chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

Produkt 1

HCID 70692775HCID 70692775, VerbindungAusbeute 47,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 10796Cesium carbonateReagenzHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

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

Quellen und Nachweise

ORD-Eintrag
ord-e0d4157f08c0492097a16f50798a4aa4
Quelldatensatz
750 AstraZeneca ELN dataset
Originallink
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