Potassium Hydroxide → HCID 53356845, compound

HRID 877467Notes

Reaction equation

HRID 877467 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][C:14]=1[Cl:15])[N:11](S(C1C=CC(C)=CC=1)(=O)=O)[C:10]1[C:9]([C:31]([F:34])([F:33])[F:32])([O:26][Si](C)(C)C)[CH:8]([F:35])[CH2:7][CH2:6][C:5]2=1.[OH-].[K+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][C:14]=1[Cl:15])[NH:11][C:10]1[C:9]([C:31]([F:32])([F:34])[F:33])([OH:26])[CH:8]([F:35])[CH2:7][CH2:6][C:5]2=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86676824HCID 86676824, compound

Product 1

HCID 53356845HCID 53356845, compoundYield 48.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To 6,7-dichloro-2-fluoro-9-tosyl-1-(trifluoromethyl)-1-(trimethylsilyloxy)-2,3,4,9-tetrahydro-1H-carbazole (0.2 g, 0.35 mmol) in THF (10 mL), KOH (98 mg, 1.7 mmol) in H2O (10 mL) was added and the resulting mixture was refluxed for 6 h. The reaction mixture was diluted with water (20 mL) and extracted with EtOAc (3×30 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography [EtOAc-hexane (1:9) as eluant] and the solid obtained was washed with cold pentane to give the title compound (58 mg, 40%). 1H NMR (500 MHz, CDCl3, δ in ppm) 8.25 (bs, 1H), 7.62 (s, 1H), 7.5 (s, 1H), 5.25-5.14 (m, 1H), 3.25 (d, J=6.5 Hz, 1H), 2.94-2.89 (m, 1H), 2.80-2.74 (m, 1H), 2.44-2.39 (m, 1H), 2.35-2.29 (m, 1H).

Workup

  1. temperaturethe resulting mixture was refluxed for 6 h
  2. extractionextracted with EtOAc (3×30 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by column chromatography [EtOAc-hexane (1:9) as eluant]
  6. customthe solid obtained
  7. washwas washed with cold pentane

Sources & evidence

ORD record
ord-aa207edc346841d398f35673ae57c6af
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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