Carbon Dioxide → 7-Fluoro-1H-indole-5-carboxylic acid

HRID 401727Notes

Reaction equation

HRID 401727 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[NH:7][CH:6]=[CH:5]2.[Li]CCCC.[C:17](=[O:19])=[O:18].O>C1COCC1>[F:11][C:9]1[CH:10]=[C:2]([C:17]([OH:19])=[O:18])[CH:3]=[C:4]2[C:8]=1[NH:7][CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 35348805-bromo-7-fluoro-1H-indoleHCID 178418339Butyllithium

Product 1

HCID 115645587-Fluoro-1H-indole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-7-fluoroindole 70f (1.71 mmol, 365 mg) in THF at −60° C. was added n-BuLi (1.6 M solution in hexanes, 5.2 mmol, 3.2 mL). The solution was kept at −60° C. for 4 h and was then poured onto an excess of freshly crushed dry ice. Water was added and the mixture was acidified to pH=4. The organic phase was concentrated and the residue was purified by flash column chromatography (silica gel, 35% EtOAc/hexanes) to give compound 70h.

Workup

  1. concentrationThe organic phase was concentrated
  2. customthe residue was purified by flash column chromatography (silica gel, 35% EtOAc/hexanes)
  3. customto give compound 70h.

Sources & evidence

ORD record
ord-d2ffffbcecbc466984aaacf61fd5162e
Source dataset
uspto-grants-2014_06
Patent number
US08741887B2

Reaction notes

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