StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Cesium carbonate → 6-(Thiazolo[4,5-b]pyridin-2-yloxy)-1H-indole-2-carboxylic acid methyl ester

HRID 1947461
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1947461
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([OH:14])[CH:8]=2)=[O:4].Cl.Cl[C:17]1[S:18][C:19]2[C:20]([N:25]=1)=[N:21][CH:22]=[CH:23][CH:24]=2.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N.CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([O:14][C:17]1[S:18][C:19]3[C:20]([N:25]=1)=[N:21][CH:22]=[CH:23][CH:24]=3)[CH:8]=2)=[O:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 10535709methyl 6-hydroxy-1H-indole-2-carboxylateHCID 574827652-Chlorothiazolo[4,5-b]pyridine hydrochloride

Produkt 1

HCID 687723426-(Thiazolo[4,5-b]pyridin-2-yloxy)-1H-indole-2-carboxylic acid methyl esterAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21891449
acetonitrile N,N-dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution 6-hydroxy-1H-indole-2-carboxylic acid methyl ester (4.0 g, 21 mmol) and 2-chloro-thiazolo[4,5-b]pyridine hydrochloride (4.3 g, 21 mmol) in MeCN:DMF (4:1, 250 mL) was added Cs2CO3 (13.8 g, 42 mmol) and the reaction mixture was heated (60° C., 4 h). The reaction mixture was cooled (rt) and partitioned between EtOAc (300 mL) and saturated NH4Cl (200 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2×200 mL). The organic layer was dried, filtered and concentrated in vacuo. The resulting residue was purified by silica gel flash chromatography using MeOH (0.2 M NH3):DCM (0-15%) to provide the title compound as a brown solid (3.6 g, 53%). MS (ESI): mass calcd. for C16H11N3O3S, 325.1; m/z found, 326.0[M+H]+. 1H NMR (400 MHz, DMSO-d6): 12.18 (s, 1H), 8.52 (dd, J=4.8, 1.7, 1H), 8.39 (dd, J=8.0, 1.7, 1H), 7.82 (d, J=8.7, 1H), 7.53 (d, J=2.2, 1H), 7.34 (dd, J=8.0, 4.8, 1H), 7.26 (dd, J=2.2, 0.9, 1H), 7.19 (dd, J=8.7, 2.2, 1H), 3.88 (s, 3H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled (rt)
  2. custompartitioned between EtOAc (300 mL) and saturated NH4Cl (200 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with EtOAc (2×200 mL)
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified by silica gel flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a3f8599e0cc0425b96e0068d23b39da8
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08399465B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion