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Hydrochloric Acid → 3-Methyl-7-azaindole

HRID 1625227
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1625227
C([Li])CCC.[CH2:6]([C:8]1[C:9]([NH:14][C:15](=O)OC(C)(C)C)=[N:10][CH:11]=[CH:12][CH:13]=1)[CH3:7].Cl.[OH-].[Na+]>C1COCC1.O.C(OCC)(=O)C.CN(C=O)C>[CH3:7][C:6]1[C:8]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[NH:14][CH:15]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11117638tert-Butyl (3-ethylpyridin-2-yl)carbamateHCID 178418339Butyllithium

Produkt 1

HCID 109314713-Methyl-7-azaindoleAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962
Water
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Normal-butyllithium (2.69 M, 118.7 mL) was dropwise added to a solution of compound (40a) (32.4 g) in THF (500 mL) at an internal temperature of −30 to −10° C., followed by stirring at 0° C. for 30 min. Subsequently, a solution of DMF (11.18 g) in THF (50 mL) was added to the reaction solution at an internal temperature of −40° C., followed by increasing the temperature to room temperature. Then, 6 N hydrochloric acid (200 mL) was added to the reaction solution, followed by stirring at 60° C. for 2 hr. After cooling, ethyl acetate (200 mL) and water (100 mL) were added to the reaction solution for distribution. The aqueous layer was added to sodium hydroxide (4 M, 300 mL), and pH was adjusted to 12, followed by stirring for 1 hr. The precipitate was collected by filtration, washed by sprinkling water, and dried under reduced pressure to obtain compound (40b) (16.52 g, 86%) as a white solid.

Aufarbeitung

  1. temperatureby increasing the temperature to room temperature
  2. stirringby stirring at 60° C. for 2 hr
  3. temperatureAfter cooling
  4. stirringby stirring for 1 hr
  5. filtrationThe precipitate was collected by filtration
  6. washwashed
  7. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-75c9bd33279e4f53b000a82788ae3a73
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08779142B2

Notizen zur Reaktion

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