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

HRID 1737828Notes

Reaction equation

HRID 1737828 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-909e0b37bb294666997fc1b3c6500c71
Source dataset
uspto-grants-1999_10
Patent number
US05962474

Reaction notes

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