Potassium Hydroxide → HCID 52943430, compound

HRID 877463Notes

Reaction equation

HRID 877463 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([Cl:15])[CH:14]=1)[NH:11][C:10]1[C:9]([C:21]([F:24])([F:23])[F:22])([O:16][Si](C)(C)C)[CH2:8][CH2:7][CH2:6][C:5]2=1.[OH-].[K+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([Cl:15])[CH:14]=1)[NH:11][C:10]1[C:9]([C:21]([F:23])([F:22])[F:24])([OH:16])[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 68264969HCID 68264969, compound

Product 1

HCID 52943430HCID 52943430, compoundYield 30.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

6,8-Dichloro-1-(trifluoromethyl)-1-(trimethylsilyloxy)-2,3,4,9-tetrahydro-1H-carbazole (0.4 g, 1.0 mmol) was dissolved in THF (5 mL) and KOH (280 mg, 5.0 mmol) in H2O (5 mL), was added. The resulting mixture stirred at room temperature for 2 h, diluted with water (20 mL) and extracted with EtOAc (3×20 mL). The combined organic extracts were then dried over Na2SO4 and concentrated under reduced pressure to give the crude residue which was purified by column chromatography [EtOAc-hexane (1:19) as eluant] to provide the title compound as a white solid (100 mg, 26%). 1H NMR (500 MHz, DMSO-d6, δ in ppm) 11.03 (s, 1H), 7.57 (d, J=1.5 Hz, 1H), 7.32 (d, J=1.5 Hz, 1H), 6.6 (s, 1H), 2.72-2.64 (m, 2H), 2.23-2.19 (m, 1H), 2.0-1.9 (m, 3H).

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. dry with materialThe combined organic extracts were then dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customto give the crude residue which
  5. customwas purified by column chromatography [EtOAc-hexane (1:19) as eluant]

Sources & evidence

ORD record
ord-cd316baf012c46bd90b5d4cfdc6095c5
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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