Methyl indole-6-carboxylate → methyl 3-fluoro-1H-indole-6-carboxylate

HRID 409915Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 409915
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.[O-]S(C(F)(F)[F:19])(=O)=O.F[N+]1C(C)=CC(C)=CC=1C>CO>[F:19][C:3]1[C:4]2[C:9](=[CH:8][C:7]([C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=2)[NH:1][CH:2]=1

Komponenten

4

Edukt 2

HCID 639844Methyl indole-6-carboxylateHCID 27245751-Fluoro-2,4,6-trimethylpyridinium Trifluoromethanesulfonate [Fluorinating Reagent]

Produkt 1

HCID 59625843methyl 3-fluoro-1H-indole-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of methyl 1H-indole-6-carboxylate 20a (11.4 mmol, 2.0 g) and N-fluoro-2,4,6-trimethylpyridinium triflate (14.8 mmol, 4.3 g) in MeOH (100 mL) was heated at reflux for 18 h. The reaction mixture was concentrated and purified by flash column chromatography (silica gel, 15-20% EtOAc/hexanes) to give compound 20b as an off-white solid.

Aufarbeitung

  1. temperatureat reflux for 18 h
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by flash column chromatography (silica gel, 15-20% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-73b9c93dbb2d4175912811e925bef103
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759533B2

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