Ethanol → HCID 53356848, compound

HRID 877474Notes

Reaction equation

HRID 877474 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH2:7][CH2:8][CH2:9][C:10]([C:30]([F:33])([F:32])[F:31])([O:25][Si](C)(C)C)[C:11]=3[N:12]2S(C2C=CC(C)=CC=2)(=O)=O)=[CH:4][C:3]=1[F:34].[OH-].[K+].CCO>C1COCC1.O>[Cl:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH2:7][CH2:8][CH2:9][C:10]([C:30]([F:33])([F:31])[F:32])([OH:25])[C:11]=3[NH:12]2)=[CH:4][C:3]=1[F:34]

Participants

6

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 67378073HCID 67378073, compound

Product 1

HCID 53356848HCID 53356848, compoundYield 44.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

7-Chloro-6-fluoro-9-tosyl-1-(trifluoromethyl)-1-(trimethylsilyloxy)-2,3,4,9-tetrahydro-1H-carbazole (0.12 g, 0.22 mmol) was dissolved in THF (5 mL) and KOH (0.064 g, 1.0 mmol), in H2O (2 mL), was added. The reaction mixture was stirred at room temperature for 30 min., followed by the addition of EtOH (2 mL) and then heated to 60° C. for 8 h, diluted with water (10 mL) and extracted with EtOAc (2×10 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to give the crude compound which was purified by column chromatography [EtOAc-hexane (1:9) as eluant] to afford the title compound as an off-white solid (0.030 g, 37%). 1H NMR (500 MHz, DMSO-d6, δ in ppm) 11.01 (s, 1H), 7.50-7.47 (m, 2H), 6.68 (s, 1H), 2.72-2.68 (m, 1H), 2.62-2.57 (m, 1H), 2.12-2.2.08 (m, 1H), 2.01-1.98 (m, 1H), 1.92-1.90 (m, 2H).

Workup

  1. temperatureheated to 60° C. for 8 h
  2. extractionextracted with EtOAc (2×10 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto give the crude compound which
  6. customwas purified by column chromatography [EtOAc-hexane (1:9) as eluant]

Sources & evidence

ORD record
ord-2afc0c16c3204ac1b634e70c9e6beae3
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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