5-Chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile → N-[1-[3-cyano-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl]indol-6-yl]-N-methylacetamide

HRID 669

Reaktionsgleichung

Reaktionsgleichung von HRID 669
CC(=O)N(C)c1ccc2cc[nH]c2c1.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>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]>CC(=O)N(C)c1ccc2ccn(-c3cc(NC4CC4)n4ncc(C#N)c4n3)c2c1

Komponenten

7

Edukt 2

HCID 898271735-Chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrileHCID 119085442N-(1H-indol-6-yl)-N-methylacetamide

Produkt 1

HCID 70682212N-[1-[3-cyano-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl]indol-6-yl]-N-methylacetamideAusbeute 15,88 %

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 microwave tube, added 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (84mg), N-(1H-indol-6-yl)-N-methylacetamide (67 mg), Pd2(dba)3 (16 mg), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (20mg) cesium carbonate(129 mg) in anhydrous DMA (0.5mL). under microwave 150C for 30 min. the mixture was filtered. washed with MeOH. combinde organic solvent, dried to dryness. The residue solid was washed with MeOH to give about 22mg offwhite solid (product.

Quellen und Nachweise

ORD-Eintrag
ord-2f0f980a972d4857b85fb2314cbcce6e
Quelldatensatz
750 AstraZeneca ELN dataset
Originallink
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