Potassium Hydroxide → HCID 53356883, compound

HRID 877505Notes

Reaction equation

HRID 877505 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7](S(C3C=CC(C)=CC=3)(=O)=O)[C:6]3[C:21]([C:29]([F:32])([F:31])[F:30])([O:24][Si](C)(C)C)[CH2:22][CH2:23][C:5]=3[C:4]=2[C:3]=1[Cl:33].[OH-].[K+]>C1COCC1.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[C:21]([C:29]([F:31])([F:30])[F:32])([OH:24])[CH2:22][CH2:23][C:5]=3[C:4]=2[C:3]=1[Cl:33]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67377997HCID 67377997, compound

Product 1

HCID 53356883HCID 53356883, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To 7,8-dichloro-4-tosyl-3-(trifluoromethyl)-3-(trimethylsilyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indole (0.2 g, 0.3 mmol) in THF (10 mL), KOH (104 mg, 1.8 mmol) in H2O (10 mL) was added and the resulting mixture was refluxed for 18 h. The reaction mixture was diluted with water (20 mL) and extracted with EtOAc (3×10 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to give the crude compound which was purified by column chromatography (10% EtOAc-hexane) to afford the title compound as a white solid (58 mg, 53%). 1H NMR (500 MHz, DMSO-d6, δ in ppm) 11.70 (s, 1H), 7.35 (d, 8.5 Hz, 1H), 7.28 (d, J=9.0 Hz, 1H), 6.90 (s, 1H), 3.12-3.07 (m, 1H), 2.97-2.88 (m, 2H), 2.88-2.50 (m, 1H).

Workup

  1. temperaturethe resulting mixture was refluxed for 18 h
  2. extractionextracted with EtOAc (3×10 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give the crude compound which
  6. customwas purified by column chromatography (10% EtOAc-hexane)

Sources & evidence

ORD record
ord-87f782124ff944a5aa9975d65e48f7f9
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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