Phenol → Phenyl-1,1-dimethyl-1H-benzo[e]indole-2-carboxylate

HRID 855935Notes

Reaction equation

HRID 855935 reaction equation
[CH3:1][C:2]1([CH3:18])[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[CH:7]=[CH:6][C:5]=2[N:4]=[C:3]1[C:15]([OH:17])=[O:16].[C:19]1(O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl>[C:19]1([O:16][C:15]([C:3]2[C:2]([CH3:18])([CH3:1])[C:10]3[C:9]4[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=4[CH:7]=[CH:6][C:5]=3[N:4]=2)=[O:17])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 996PhenolHCID 115577531,1-dimethyl-1H-benzo[e]indole-2-carboxylic acid

Product 1

HCID 12136804Phenyl-1,1-dimethyl-1H-benzo[e]indole-2-carboxylateYield 2.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

200 mg of 1,1-dimethyl-1H-benzo[e]indole-2-carboxylic acid 3 (0.84 mmol) and 395 mg (4.2 mmol) phenol were dissolved in 50 mL methylene chloride. Then 188 μL (1.12 mmol) trifluorosulfonic acid anhydride were added and the reaction mixture was stirred at room temperature for 5 hours. After evaporation of the solvent under reduced pressure, the residue was taken up in methylene chloride and washed with 0.1 N NaOH and water. The organic phase was separated, dried over sodium sulfate and filtered. The solvent was removed under vacuum and the crude product was purified by preparative HPLC column chromatography (eluent: water-acetonitrile). The appropriate fractions were combined and dried by lyophilization to yield 7.5 mg of product 4.

Workup

  1. customAfter evaporation of the solvent under reduced pressure
  2. washwashed with 0.1 N NaOH and water
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under vacuum
  7. customthe crude product was purified by preparative HPLC column chromatography (eluent: water-acetonitrile)
  8. customdried by lyophilization

Sources & evidence

ORD record
ord-b9203654e9134c109b82def0fb251663
Source dataset
uspto-grants-2007_08
Patent number
US07262306B2

Reaction notes

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