Potassium Hydroxide → HCID 53356869, compound

HRID 877500Notes

Reaction equation

HRID 877500 reaction equation
[Cl:1][C:2]1[C:3]([Cl:33])=[CH:4][C:5]2[C:6]3[CH2:23][CH2:22][C:21]([C:29]([F:32])([F:31])[F:30])([O:24][Si](C)(C)C)[C:7]=3[N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:9]=2[CH:10]=1.[OH-].[K+]>C1COCC1.O>[Cl:1][C:2]1[C:3]([Cl:33])=[CH:4][C:5]2[C:6]3[CH2:23][CH2:22][C:21]([C:29]([F:31])([F:30])[F:32])([OH:24])[C:7]=3[NH:8][C:9]=2[CH:10]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 71253482HCID 71253482, compound

Product 1

HCID 53356869HCID 53356869, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

6,7-Dichloro-4-tosyl-3-(trifluoromethyl)-3-(trimethylsilyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indole (0.2 g, 0.37 mmol) was dissolved in THF (10 mL) and 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 (10 mL) and extracted with EtOAc (3×20 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to give the crude compound which was purified by column chromatography [EtOAc-hexane (3:17) as eluant] to afford the title compound (58 mg, 52%). 1H NMR (500 MHz, CDCl3, δ in ppm) 8.05 (bs, 1H), 7.62 (s, 1H), 7.49 (s, 1H), 3.12-3.07 (m, 1H), 3.04-2.99 (m, 1H), 2.91-2.86 (m, 1H), 2.57-2.55 (m, 1H), 2.51 (s, 1H).

Workup

  1. temperaturethe resulting mixture was refluxed for 18 h
  2. extractionextracted with EtOAc (3×20 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 [EtOAc-hexane (3:17) as eluant]

Sources & evidence

ORD record
ord-a76ed4bad72840c0a6b2155284877c8b
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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