5-Azaindole → 3-Chloro-1H-pyrrolo[3,2-c]pyridine

HRID 2201812Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2201812
[NH:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=[CH:2]1.[Cl:10]N1C(=O)CCC1=O>ClCCl>[Cl:10][C:3]1[C:4]2[CH:5]=[N:6][CH:7]=[CH:8][C:9]=2[NH:1][CH:2]=1

Komponenten

4

Edukt 2

HCID 92205-AzaindoleHCID 31398Chlorosuccinimide

Produkt 1

HCID 247292153-Chloro-1H-pyrrolo[3,2-c]pyridineAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 1H-pyrrolo[3,2-c]pyridine (200 mg, 1.69 mmol) in dichloromethane (10 mL) was treated with N-chlorosuccinimide (332 mg, 2.5 mmol) and stirred at room temperature for about 5 hours. The reaction mixture was diluted with dichloromethane and washed with aq. sodium hydrogen carbonate solution, brine, dried over anhydrous sodium sulphate and concentrated. Purification by silica gel (100-200) column chromatography using methanol and dichloromethane gradient as eluent afforded 3-chloro-1H-pyrrolo[3,2-c]pyridine (103 mg, 40%).

Aufarbeitung

  1. washwashed with aq. sodium hydrogen carbonate solution, brine
  2. dry with materialdried over anhydrous sodium sulphate
  3. concentrationconcentrated
  4. customPurification by silica gel (100-200) column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-deb76b152878457689098d5831539c3a
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09364466B2

Notizen zur Reaktion

Wird geladen…