Cesium carbonate → 5-(4-(Morpholinomethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

HRID 336406

Reaktionsgleichung

Reaktionsgleichung von HRID 336406
CC1(C)C(C)(C)OB([C:9]2[CH:21]=[CH:20][C:12]([CH2:13][N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[CH:11][CH:10]=2)O1.Br[C:24]1[N:29]2[N:30]=[C:31]([NH2:33])[N:32]=[C:28]2[CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(COC)OC.O>C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[O:17]1[CH2:16][CH2:15][N:14]([CH2:13][C:12]2[CH:11]=[CH:10][C:9]([C:24]3[N:29]4[N:30]=[C:31]([NH2:33])[N:32]=[C:28]4[CH:27]=[CH:26][CH:25]=3)=[CH:21][CH:20]=2)[CH2:19][CH2:18]1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 27955024-((Morpholino)methyl)phenylboronic acid pinacol esterHCID 18180031Water 1,2-dimethoxyethaneHCID 252159395-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Produkt 1

HCID 591864835-(4-(Morpholinomethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amineAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)morpholine (1.9 g, 6.3 mmol), 5-bromo-[1,2,4]triazolo[1,5-a]pyridine-2-amine (1 g, 5 mmol), 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) chloride (250 mg, 0.63 mmol), and cesium carbonate (4.1 g, 12.6 mmol) in 10:1 dimethoxyethane/water (11 mL) was heated at 140° C. under microwave radiation for 1 h. The reaction mixture was diluted with ethyl acetate (200 mL), and the resulting suspension was filtered through celite. The filtrate was concentrated, and the resulting residue was purified by flash column chromatography (petroleum ether→ethyl acetate) to provide product (1 g, 69% yield). LCMS (ESI) m/z: 310.

Aufarbeitung

  1. filtrationthe resulting suspension was filtered through celite
  2. concentrationThe filtrate was concentrated
  3. customthe resulting residue was purified by flash column chromatography (petroleum ether→ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-a2eeac91b4f04a35975b2331edd9176d
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889673B2

Verknüpfte Notizen

Wird geladen…