Triethylamine → 4-fluoro-N-(1H-indol-5-yl)benzamide

HRID 843877Notes

Reaction equation

HRID 843877 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C(N(CC)CC)C.[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1.[OH-].[Na+]>O1CCCC1.O>[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[CH:5]3)=[O:24])=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 678794-Fluorobenzoyl chlorideHCID 788675-Aminoindole

Product 1

HCID 28145064-fluoro-N-(1H-indol-5-yl)benzamideYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3.96 gm (30.0 mMol) 5-amino-1H-indole in 150 mL tetrahydrofuran were added 5.6 mL triethylamine followed by a solution of 5.2 gm (33.0 mMol) 4-fluorobenzoyl chloride in 30 mL tetrahydrofuran. After 18 hours the reaction mixture was poured into water, made basic with sodium hydroxide solution, and extracted with dichloromethane. The organic extracts were combined, dried over sodium sulfate and concentrated under reduced pressure to give a purple solid. This residue was recrystallized from ethyl acetate/hexane to give 6.37 gm (84%) 5-(4-fluoro-benzoyl)amino-1H-indole as brown crystals in two crops.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a purple solid
  5. customThis residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-1db0d8870a94446dbebb76edc28c15fc
Source dataset
uspto-grants-2002_04
Patent number
US06380201B1

Reaction notes

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