Potassium Hydroxide → HCID 52946488, compound

HRID 877465Notes

Reaction equation

HRID 877465 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[NH:7][C:6]1[C:12]([C:22]([F:25])([F:24])[F:23])([O:17][Si](C)(C)C)[CH2:13][CH2:14][CH2:15][CH2:16][C:5]2=1.[OH-].[K+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[NH:7][C:6]1[C:12]([C:22]([F:24])([F:25])[F:23])([OH:17])[CH2:13][CH2:14][CH2:15][CH2:16][C:5]2=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67363076HCID 67363076, compound

Product 1

HCID 52946488HCID 52946488, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

2,4-Dichloro-6-(trifluoromethyl)-6-(trimethylsilyloxy)-5,6,7,8,9,10-hexahydrocyclohepta[b]indole (0.3 g, 7.0 mmol) was dissolved in THF (5 mL) and KOH (0.2 g, 3.6 mmol) in water (5 mL) was added to the mixture. The reaction mixture was refluxed for 1 h and then cooled to room temperature, diluted with water and extracted with EtOAc (3×20 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography [EtOAc-hexane (1:17) as eluant] to furnish the title compound as a pale yellow solid (0.05 g, 21%). 1H NMR (500 MHz, CDCl3, δ in ppm) 8.67 (br s, 1H), 7.43 (d, J=1.5 Hz, 1H), 7.41 (d, J=1.5 Hz, 1H), 2.9 (m, 1H), 2.73 (m, 1H), 2.49 (s, 1H) 2.43-2.4 (m, 1H), 2.08-2.03 (m, 4H), 1.16-1.54 (m, 1H)

Workup

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. extractionextracted with EtOAc (3×20 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was purified by silica gel chromatography [EtOAc-hexane (1:17) as eluant]

Sources & evidence

ORD record
ord-f4e705ad105f469097f128924d158c57
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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