Cesium carbonate → (2-Chloro-pyridin-4-yl)-(5-cyclopropyl-1H-pyrazole-3-yl)-amine

HRID 75921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 75921
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([Cl:8])[CH:3]=1.C(OC([N:16]1[C:20]([CH:21]2[CH2:23][CH2:22]2)=[CH:19][C:18]([NH2:24])=[N:17]1)=O)(C)(C)C.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:8][C:4]1[CH:3]=[C:2]([NH:24][C:18]2[CH:19]=[C:20]([CH:21]3[CH2:23][CH2:22]3)[NH:16][N:17]=2)[CH:7]=[CH:6][N:5]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 15165112-Chloro-4-iodopyridineHCID 11218347tert-butyl 3-amino-5-cyclopropyl-1H-pyrazole-1-carboxylate

Produkt 1

HCID 86620618(2-Chloro-pyridin-4-yl)-(5-cyclopropyl-1H-pyrazole-3-yl)-amineAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 4-iodo-2-chloropyridine (0.26 g, 1.1 mmol), 3-amino-5-cyclopropyl-pyrazole-1-carboxylic acid tert-butyl ester (0.20 g, 0.89 mmol), Pd2 dba3 (0.016 g, 2 mol %), Xantphos (0.031 g, 6 mol %), and Cs2CO3 (0.41 g, 1.3 mmol) in degassed toluene (4 ml) was purged with N2 and heated to 100° C. in a sealed tube for 2 days. The mixture was diluted with THF and filtered to remove Cs2CO3. The filtrate was concentrated under reduced pressure and purified by column chromatography (hexane-EtOAc=3:1) to give the title compound (0.10 g, 48%). MS: Calcd.: 234. Found: [M+H]+ 235.

Aufarbeitung

  1. customwas purged with N2
  2. additionThe mixture was diluted with THF
  3. filtrationfiltered
  4. customto remove Cs2CO3
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. custompurified by column chromatography (hexane-EtOAc=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-003cbea543f74ba8aa8ddb5f0d572428
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835465B2

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