Sodium Hydroxide → 5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acid

HRID 2041929Notes

Reaction equation

HRID 2041929 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)[C:8]([C:21]([O:23]CC)=[O:22])=[CH:7]2>O.C(O)C>[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)[C:8]([C:21]([OH:23])=[O:22])=[CH:7]2

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 57431514Ethyl 5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylate

Product 1

HCID 574315135-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

An aqueous solution of sodium hydroxide, prepared from 1.15 g (28.92 mmol) of sodium hydroxide pellets in 50 ml of water, is added to a solution of 7.6 g (24.10 mmol) of ethyl 5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylate (WO 2006/024776) in 241 ml of ethanol. The mixture is heated for two hours and then concentrated under reduced pressure. The resulting solid is taken up in 200 ml of water. The solution is washed with twice 100 ml of ethyl ether, acidified by successive additions of small amounts of concentrated hydrochloric acid, and then extracted with 200 ml of ethyl acetate. The organic phase is finally washed twice with 100 ml of water and once with 50 ml of a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. After drying at 50° C. under reduced pressure, 6.4 g of the expected product are obtained in the form of a solid, which will be used as it is in the next step.

Workup

  1. temperatureThe mixture is heated for two hours
  2. concentrationconcentrated under reduced pressure
  3. washThe solution is washed with twice 100 ml of ethyl ether
  4. extractionextracted with 200 ml of ethyl acetate
  5. washThe organic phase is finally washed twice with 100 ml of water and once with 50 ml of a saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. dry with materialAfter drying at 50° C. under reduced pressure, 6.4 g of the expected product
  9. customare obtained in the form of a solid, which

Sources & evidence

ORD record
ord-b0121df4eeef4bca9c57ff2903257712
Source dataset
uspto-grants-2013_11
Patent number
US08586573B2

Reaction notes

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