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

HRID 409915

Reaction equation

HRID 409915 reaction equation
[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

Participants

4

Reactant 2

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

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 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.

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-73b9c93dbb2d4175912811e925bef103
Source dataset
uspto-grants-2014_06
Patent number
US08759533B2

Linked notes

Loading…