1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-Methyl-5-phenyl-1H-pyrrolo[2,3-c]pyridine

HRID 400605Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 400605
C(OC(=O)[NH:7][C:8]1[CH:9]=[N:10][C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][C:13]=1[C:14]#[C:15][CH3:16])(C)(C)C.C1CCN2C(=NCCC2)CC1>CO.O>[CH3:16][C:15]1[NH:7][C:8]2=[CH:9][N:10]=[C:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:12]=[C:13]2[CH:14]=1

Komponenten

5

Edukt 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 60026785(6-Phenyl-4-prop-1-ynylpyridin-3-yl)carbamic acid tert-butyl ester

Produkt 1

HCID 600266192-Methyl-5-phenyl-1H-pyrrolo[2,3-c]pyridineAusbeute 99,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of (6-phenyl-4-prop-1-ynylpyridin-3-yl)carbamic acid tert-butyl ester (670 mg, 2.17 mmol) in a mixture of 33 mL of methanol and 11 mL of water was treated with DBU (2.0 mL, 13.4 mmol). The resulting mixture was heated at 60° C. After 24 hours, the mixture was concentrated in vacuo, 50 mL of water was added, the mixture was sonicated, and the resulting solid was filtered. The solid was dried over P2O5 in vacuum to give 450 mg of the title product as a yellow solid (99% yield), which was used without further purification.

Aufarbeitung

  1. concentrationthe mixture was concentrated in vacuo, 50 mL of water
  2. additionwas added
  3. customthe mixture was sonicated
  4. filtrationthe resulting solid was filtered
  5. dry with materialThe solid was dried over P2O5 in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1ad0635c51564572aea0371a72359b89
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741897B2

Notizen zur Reaktion

Wird geladen…