Potassium Hydroxide → HCID 49821197, compound

HRID 877457Notes

Reaction equation

HRID 877457 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)[CH2:8][CH2:7][CH2:6][C:5]2=1.[OH-].[K+]>C1COCC1.CCO.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:33])[F:34])([OH:26])[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67377386HCID 67377386, compound

Product 1

HCID 49821197HCID 49821197, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

6,7-Dichloro-9-tosyl-1-(trifluoromethyl)-1-(trimethylsilyloxy)-2,3,4,9-tetrahydro-1H-carbazole (220 mg, 0.41 mmol) was dissolved in anhydrous THF-EtOH (10 mL, 1:1). KOH (117 mg, 2.06 mmol) in H2O (7 mL) was added and then stirred at room temperature for 30 min. and then at 55° C. for 20 h. The reaction mixture was diluted with water (30 mL) and extracted with EtOAc (3×20 mL). The combined organic extracts were dried over Na2SO4 and the solvent was removed under reduced pressure to provide the crude compound which was purified by column chromatography [EtOAc-hexane (1:9) as eluant] to afford the title compound as a white solid (130 mg, 76%). 1H NMR (500 MHz. DMSO-d6, δ in ppm) 8.17 (bs, 1H), 7.61 (s, 1H), 7.48 (s, 1H), 2.82-2.78 (m, 1H), 2.70-2.64 (m, 1H), 2.42 (s, 1H), 2.28-2.20 (m, 1H), 2.12-2.01 (m, 3H).

Workup

  1. waitat 55° C. for 20 h
  2. extractionextracted with EtOAc (3×20 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. customthe solvent was removed under reduced pressure
  5. customto provide the crude compound which
  6. customwas purified by column chromatography [EtOAc-hexane (1:9) as eluant]

Sources & evidence

ORD record
ord-a641046baa2f4484a01cac0e016c5f2d
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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