4-Fluorobenzoyl chloride → HCID 18971832, compound

HRID 843931Notes

Reaction equation

HRID 843931 reaction equation
C([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]1[CH2:16][CH2:15][CH:14]([N:22]([CH3:24])[CH3:23])[CH2:13][C:12]2=1)=O)(C)(C)C.[F:25][C:26]1[CH:34]=[CH:33][C:29](C(Cl)=O)=[CH:28][CH:27]=1>FC(F)(F)C(O)=O>[F:25][C:26]1[CH:34]=[CH:33][C:29]([C:6]([NH:8][C:9]2[CH:10]=[C:11]3[C:19](=[CH:20][CH:21]=2)[NH:18][C:17]2[CH2:16][CH2:15][CH:14]([N:22]([CH3:23])[CH3:24])[CH2:13][C:12]3=2)=[O:5])=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 54055691HCID 54055691, compound

Product 1

HCID 18971832HCID 18971832, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 0.10 gm (0.30 mMol) 6-(t-butoxycarbonyl)amino-3-(dimethyl)amino-1,2,3,4-tetrahydro-9H-carbazole in 1.0 mL trifluoroacetic acid was stirred for 20 minutes at room temperature. The reaction mixture was then concentrated under reduced pressure. The residual oil was then dissolved in 5 mL tetrahydrofuran. To this solution was added 1.5 mL triethylamine followed by 5.0 μL (0.42 mMol) 4-fluorobenzoyl chloride and the solution was stirred for 1 hour at room temperature. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in dichloromethane. This solution was washed with aqueous potassium carbonate and was then concentrated under reduced pressure. The residue was dissolved in dilute aqueous tartaric acid and the solution was extracted well with dichloromethane. The remaining aqueous phase was made basic with dilute aqueous sodium hydroxide and was extracted well with dichloromethane. These organic phases were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 95:5 chloroform:5% ammonium hydroxide in methanol. Fractions containing the product were combined and concentrated under reduced pressure to give 0.102 gm (95%) of 6-(4-fluorobenzoyl)amino-3-(dimethyl)amino-1,2,3,4-tetrahydro-9H-carbazole.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. dissolutionThe residual oil was then dissolved in 5 mL tetrahydrofuran
  3. additionTo this solution was added 1.5 mL triethylamine
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. dissolutionthe residue was dissolved in dichloromethane
  6. washThis solution was washed with aqueous potassium carbonate
  7. concentrationwas then concentrated under reduced pressure
  8. dissolutionThe residue was dissolved in dilute aqueous tartaric acid
  9. extractionthe solution was extracted well with dichloromethane
  10. extractionwas extracted well with dichloromethane
  11. dry with materialdried over sodium sulfate
  12. concentrationconcentrated under reduced pressure
  13. washeluting with 95:5 chloroform
  14. additionFractions containing the product
  15. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5b0107d902274fc6be38671d14ffa650
Source dataset
uspto-grants-2002_04
Patent number
US06380201B1

Reaction notes

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