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N,N'-Dimethylethylenediamine → tert-butyl 4-[1-methyl-6-(pyridin-2-ylmethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]-3-oxopiperazine-1-carboxylate

HRID 1622883
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1622883
Br[C:2]1[C:10]2[C:5](=[N:6][C:7]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[CH:8][CH:9]=2)[N:4]([CH3:19])[CH:3]=1.[O:20]=[C:21]1[NH:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>[Cu]I.O.O1CCOCC1>[CH3:19][N:4]1[C:5]2=[N:6][C:7]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[CH:8][CH:9]=[C:10]2[C:2]([N:26]2[CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28])[CH2:22][C:21]2=[O:20])=[CH:3]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylateHCID 678161163-Bromo-1-methyl-6-(2-pyridylmethoxy)pyrrolo[2,3-b]pyridine

Produkt 1

HCID 67817033tert-butyl 4-[1-methyl-6-(pyridin-2-ylmethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]-3-oxopiperazine-1-carboxylate
Ausbeute 88,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 3-bromo-1-methyl-6-(pyridin-2-ylmethoxy)-1H-pyrrolo[2,3-b]pyridine (0.226 g, 0.71 mmol), tert-butyl 3-oxopiperazine-1-carboxylate (0.20 g, 1 mmol), copper (I) iodide (0.027 g, 0.142 mmol) and potassium phosphate (0.212 g, 1 mmol) is purged under a nitrogen atmosphere in a reaction tube. 1,4-Dioxane (3 mL) and N,N′-dimethylethylene diamine (0.031 mL, 0.288 mmol) are added, the tube sealed and the reaction mixture heated at 100° C. for 25 h. The reaction is cooled to room temperature, poured into water and extracted with EtOAc. The organic phase is dried over sodium sulphate, filtered and concentrated in vacuo. The residue is purified by column chromatography on silica eluting with hexane/EtOAc (1:1), followed by neat EtOAc, to give the title compound (0.275 g, 0.629 mmol) as a pale yellow solid. MS (m/z): 438 (M+1).

Aufarbeitung

  1. customis purged under a nitrogen atmosphere in a reaction tube
  2. customthe tube sealed
  3. temperatureThe reaction is cooled to room temperature
  4. extractionextracted with EtOAc
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by column chromatography on silica eluting with hexane/EtOAc (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-47d3311da1d04c9a894a4162a7096a65
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08778946B2

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