Potassium Hydroxide → HCID 52945095, compound

HRID 877479Notes

Reaction equation

HRID 877479 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([Cl:15])[CH:14]=1)[NH:11][C:10]1[C:9]([C:21]([F:24])([F:23])[F:22])([O:16][Si](C)(C)C)[C:8]([F:26])([F:25])[CH2:7][CH2:6][C:5]2=1.[OH-].[K+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([Cl:15])[CH:14]=1)[NH:11][C:10]1[C:9]([C:21]([F:22])([F:23])[F:24])([OH:16])[C:8]([F:25])([F:26])[CH2:7][CH2:6][C:5]2=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 87378397HCID 87378397, compound

Product 1

HCID 52945095HCID 52945095, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

6,8-Dichloro-2,2-difluoro-1-(trifluoromethyl)-1-(trimethylsilyloxy)-2,3,4,9-tetrahydro-1H-carbazole (0.12 g, 0.27 mmol) was dissolved in THF (5 mL) and KOH (0.055 g, 1.1 mmol) in water (5 mL) was added. The reaction mixture was stirred at room temperature for 2 h, diluted with water (10 mL) and extracted with EtOAc (2×50 mL). The combined organic extracts were dried over Na2SO4, concentrated under reduced pressure to give the crude material which was purified by column chromatography [EtOAc-hexane (1:9) as eluant] to furnish the title compound. (0.012 g, 12%). 1H NMR (500 MHz, CDCl3, δ in ppm) 8.41 (br s, 1H), 7.44 (s, 1H), 7.3 (s, 1H), 3.35 (br s, 1H), 2.97 (t, J=12.0 Hz, 2H), 2.61-2.54 (m, 2H).

Workup

  1. extractionextracted with EtOAc (2×50 mL)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customto give the crude material which
  5. customwas purified by column chromatography [EtOAc-hexane (1:9) as eluant]

Sources & evidence

ORD record
ord-b0d8297c43514200ad21352622660f0a
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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