Potassium Hydroxide → HCID 86676832, compound

HRID 877510Notes

Reaction equation

HRID 877510 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1([O:22][Si](C)(C)C)[C:15]2[NH:14][C:13]3[C:8](=[CH:9][C:10]([C:20]#[N:21])=[CH:11][C:12]=3[C:16]([F:19])([F:18])[F:17])[C:7]=2[CH2:6][CH2:5][CH2:4]1.[OH-].[K+]>C1COCC1.O>[OH:22][C:3]1([C:2]([F:28])([F:1])[F:27])[C:15]2[NH:14][C:13]3[C:8](=[CH:9][C:10]([C:20]#[N:21])=[CH:11][C:12]=3[C:16]([F:17])([F:18])[F:19])[C:7]=2[CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86676833HCID 86676833, compound

Product 1

HCID 86676832HCID 86676832, compoundYield 37.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

1,8-bis(Trifluoromethyl)-1-(trimethylsilyloxy)-2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile (100 mg, 0.23 mmol) was dissolved in THF (5 mL) and KOH (66 mg, 1.19 mmol), in H2O (5 mL), was added. The reaction mixture was stirred at room temperature for 1 h, 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 (17:3) as eluant] to afford the title compound as a white solid (30 mg, 36.58%). 1H NMR (500 MHz, CDCl3, δ in ppm) 8.75 (br s, 1H), 8.067 (s, 1H), 7.75 (s, 1H), 2.91-2.86 (m, 1H), 2.80-2.74 (m, 1H), 2.55 (s, 1H), 2.37-2.32 (m, 1H), 2.16-2.05 (m, 3H).

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customto give the crude compound which
  5. customwas purified by column chromatography [EtOAc-hexane (17:3) as eluant]

Sources & evidence

ORD record
ord-0fb71045f2ce4f5d8185f27524b0f0f0
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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