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1-(Trimethylsilyl)prop-1-yne → 5-Bromo-3,4-dimethyl-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1626006
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1626006
[Br:1][C:2]1[C:3]([CH3:10])=[C:4](I)[C:5]([NH2:8])=[N:6][CH:7]=1.C([O-])(=O)C.[K+].[Cl-].[Li+].[CH3:18][Si:19]([CH3:24])([CH3:23])[C:20]#[C:21][CH3:22]>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[C:3]([CH3:10])=[C:4]2[C:21]([CH3:22])=[C:20]([Si:19]([CH3:24])([CH3:23])[CH3:18])[NH:8][C:5]2=[N:6][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 803631-(Trimethylsilyl)prop-1-yneHCID 433294Lithium ChlorideHCID 517044Potassium AcetateHCID 401518975-Bromo-3-iodo-4-methylpyridin-2-amine

Produkt 1

HCID 670776815-Bromo-3,4-dimethyl-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845
palladium(II) acetate
Katalysator
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

The compound obtained in step 1 of Example 36 (1.8 g) was dissolved in N,N-dimethylformamide (40 ml), and potassium acetate (1.7 g) and lithium chloride (0.3 g) were added. After replacing the atmosphere in the system with nitrogen, palladium acetate (0.13 g) and 1-trimethylsilyl-1-propyne (4.3 ml) were added and the mixture was stirred at 90° C. for three days. The reaction solution was cooled to room temperature and then N,N-dimethylformamide was distilled off. The resulting residue was diluted with ethyl acetate and then washed with brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated to give the crude title compound (2.4 g).

Aufarbeitung

  1. additionwere added
  2. temperatureThe reaction solution was cooled to room temperature
  3. distillationN,N-dimethylformamide was distilled off
  4. additionThe resulting residue was diluted with ethyl acetate
  5. washwashed with brine
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-fb74b887dfaf48ffb0bb0e3d14084ed4
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08785438B2

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