Sulfuric Acid → ethyl 4-chloro-1H-pyrrolo[3,2-c]pyridine-7-carboxylate

HRID 733737

Reaktionsgleichung

Reaktionsgleichung von HRID 733737
[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][N:10](CC3C=CC(OC)=CC=3)[C:6]=2[C:5]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:4][N:3]=1.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(O)(C(F)(F)F)=O.C1(OC)C=CC=CC=1>[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][NH:10][C:6]=2[C:5]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:4][N:3]=1

Komponenten

6

Edukt 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 57840887Ethyl 4-chloro-1-{[4-(methyloxy)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridine-7-carboxylate

Produkt 1

HCID 57840913ethyl 4-chloro-1H-pyrrolo[3,2-c]pyridine-7-carboxylateAusbeute 37,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6422Trifluoroacetic acidLösungsmittelHCID 7519AnisoleLösungsmittel

Versuchsvorschrift

A solution of ethyl 4-chloro-1-{[4-(methyloxy)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridine-7-carboxylate (2.00 g) in TFA (30 ml), anisole (1.84 ml), and sulphuric acid (15 ml) was stirred at room temperature for 30 minutes. The solution was added to an aqueous saturated sodium bicarbonate solution at 0° C. and extracted with ethyl acetate. The aqueous layer was separated and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated to afford the title compound as a brown solid (0.49 g).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. customThe aqueous layer was separated
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-7a8e7dc281884b689847404ccfcb578d
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07589206B2

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