Ammonia → 5-Fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxamide

HRID 1691607

Reaction equation

HRID 1691607 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[C:6]([C:19]([OH:21])=O)=[CH:5]2.S(Cl)(Cl)=O.[NH3:26]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[C:6]([C:19]([NH2:26])=[O:21])=[CH:5]2

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 574315135-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acid

Product 1

HCID 668456965-Fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxamideYield 29.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension, stirred at 20° C., of 2 g (6.96 mmol) of 5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acid, prepared according to the protocol described in step 1.1, in 80 ml of dry toluene is admixed with 5.08 ml (69.62 mmol) of thionyl chloride. The reaction mixture is stirred at reflux for 2 hours and then concentrated under reduced pressure. The resulting product is taken up in 10 ml of dichloromethane and this solution is poured dropwise into a solution of 9.12 ml (69.62 mmol) of 30% aqueous ammonia. The reaction mixture is stirred at 20° C. for 14 hours. After this time a solid is recovered by filtration and triturated in 50 ml of diisopropyl ether. Filtration and drying under reduced pressure give 0.58 g of expected product.

Workup

  1. customprepared
  2. temperatureat reflux for 2 hours
  3. concentrationconcentrated under reduced pressure
  4. stirringThe reaction mixture is stirred at 20° C. for 14 hours
  5. filtrationAfter this time a solid is recovered by filtration
  6. customtriturated in 50 ml of diisopropyl ether
  7. filtrationFiltration
  8. customdrying under reduced pressure

Sources & evidence

ORD record
ord-fa6bd15c00ac4b898eb0f8846c2add89
Source dataset
uspto-grants-2012_04
Patent number
US08153796B2

Linked notes

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