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

HRID 2038430Notes

Reaction equation

HRID 2038430 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-d479a40b1f8c4941a0e3f58a10d769a4
Source dataset
uspto-grants-2013_11
Patent number
US08575363B2

Reaction notes

Loading…