1-Fluoro-2,4,6-trimethylpyridinium Trifluoromethanesulfonate [Fluorinating Reagent] → methyl 3-fluoro-1H-indole-6-carboxylate

HRID 403310

Reaction equation

HRID 403310 reaction equation
N1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)C=C1.[O-]S([C:18]([F:21])(F)F)(=O)=O.F[N+:23]1C(C)=CC(C)=C[C:24]=1C>CO>[F:21][C:18]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[NH:23][CH:24]=1

Participants

4

Reactant 2

HCID 27245751-Fluoro-2,4,6-trimethylpyridinium Trifluoromethanesulfonate [Fluorinating Reagent]HCID 2737635methyl 1H-indole-5-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 1H-indole-6-carboxylate 19a (2.0 g, 11.4 mmol) and N-fluoro-2,4,6-trimethylpyridinium triflate (4.3 g, 14.8 mmol) 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 21a as an off-white solid.

Workup

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

Sources & evidence

ORD record
ord-2fd051ffcbec40acb49b81de1301ba0c
Source dataset
uspto-grants-2014_06
Patent number
US08748417B2

Linked notes

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