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

HRID 409917Notes

Reaction equation

HRID 409917 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 21a (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 21b.

Workup

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

Sources & evidence

ORD record
ord-47543504fd2c42708ccdf1b3e4a638c6
Source dataset
uspto-grants-2014_06
Patent number
US08759533B2

Reaction notes

Loading…