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Cesium carbonate → 3-[2-(Pyrrolidin-1-yl)ethoxy]aniline

HRID 273521
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 273521
ClC1C=CC(OC)=CC=1C1C=C(C)C2[N:14]=C(N)N=NC=2C=1.Br[C:23]1[CH:24]=[C:25]([CH:34]=[CH:35][CH:36]=1)[O:26][CH2:27][CH2:28][N:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)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]>[N:29]1([CH2:28][CH2:27][O:26][C:25]2[CH:24]=[C:23]([NH2:14])[CH:36]=[CH:35][CH:34]=2)[CH2:33][CH2:32][CH2:31][CH2:30]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 10796Cesium carbonateHCID 211452Pyrrolidine, 1-(2-(m-bromophenoxy)ethyl)-HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 248227537-(2-Chloro-5-methoxyphenyl)-5-methylbenzo[e][1,2,4]triazin-3-amine

Produkt 1

HCID 219416963-[2-(Pyrrolidin-1-yl)ethoxy]anilineAusbeute 154,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Versuchsvorschrift

In a dry 25 mL round bottom flask, 7-(2-chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine (0.113 g, 0.377 mmol, 1 equiv), 1-[2-(3-bromo-phenoxy)-ethyl]-pyrrolidine (0.153 g, 0.565 mmol, 1.5 equiv), cesium carbonate (0.368 g, 1.13 mmol, 3 equiv), 4,5-bis(diphenylphosphino)-9,9-dimethyl xanthene (0.044 g, 0.0753 mmol, 0.2 equiv) and tris(dibenzylideneacetone)dipalladium (0.034 g, 0.0376 mmol, 0.1 equiv) were combined. The reactants were flushed with argon, diluted with dioxane (8 mL) and outfitted with reflux condenser. The reaction was heated to reflux for 18 hours, then filtered hot and the solvents were diluted with ethyl acetate and washed with brine. The brine layer was back extracted once with fresh ethyl acetate. The organic phases were combined and dried over sodium sulfate (Na2SO4). Filtration followed by evaporation and column chromatography (1:5 MeOH/DCM) provided desired product as a yellow powder (0.12 g, 65% yield). MS (ESI+): m/z=491.1, LC retention time: 2.94 min.

Aufarbeitung

  1. customThe reactants were flushed with argon
  2. additiondiluted with dioxane (8 mL)
  3. temperaturewith reflux condenser
  4. temperatureThe reaction was heated
  5. temperatureto reflux for 18 hours
  6. filtrationfiltered hot
  7. additionthe solvents were diluted with ethyl acetate
  8. washwashed with brine
  9. extractionThe brine layer was back extracted once with fresh ethyl acetate
  10. dry with materialdried over sodium sulfate (Na2SO4)
  11. filtrationFiltration
  12. customfollowed by evaporation and column chromatography (1:5 MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-86865a04a5784582bfee1c745c2ca246
Quelldatensatz
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07456176B2

Notizen zur Reaktion

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