Potassium Hydroxide → HCID 53356849, compound

HRID 877477Notes

Reaction equation

HRID 877477 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([F:28])[CH:5]=[C:6]2[C:14]=1[NH:13][C:12]1[C:11]([C:20]([F:23])([F:22])[F:21])([O:15][Si](C)(C)C)[CH:10]([C:24]([F:27])([F:26])[F:25])[CH2:9][CH2:8][C:7]2=1.[OH-].[K+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([F:28])[CH:5]=[C:6]2[C:14]=1[NH:13][C:12]1[C:11]([C:20]([F:22])([F:23])[F:21])([OH:15])[CH:10]([C:24]([F:27])([F:25])[F:26])[CH2:9][CH2:8][C:7]2=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86676825HCID 86676825, compound

Product 1

HCID 53356849HCID 53356849, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

8-Chloro-6-fluoro-1,2-bis(trifluoromethyl)-1-(trimethylsilyloxy)-2,3,4,9-tetrahydro-1H-carbazole (0.2 g, 0.44 mmol) was dissolved in THF (10 mL) and KOH (0.125 g, 2.2 mmol), water (2 mL), was added. The reaction mixture was stirred at room temperature for 2 h, diluted with water (25 mL) and extracted with EtOAc (2×25 mL). The combined organic extracts were dried over Na2SO4, concentrated in vacuo and purified by column chromatography [EtOAc-hexane (1:19) as eluant] to obtain the title compound (0.070 g, 42%) (HPLC 99%). 1H NMR (500 MHz, CDCl3, δ in ppm) 8.49 (br s, 1H), 7.26-7.23 (d, J=11.0 Hz, 1H), 7.14-7.11 (dd, J=8.5, 2.0 Hz, 1H), 3.71-3.67 (m, 1H), 2.60-2.57 (m, 1H), 5.54 (s, 1H), 2.40-2.37 (m, 1H), 2.30-2.24 (m, 1H), 2.10-2.07 (m, 1H).

Workup

  1. extractionextracted with EtOAc (2×25 mL)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by column chromatography [EtOAc-hexane (1:19) as eluant]

Sources & evidence

ORD record
ord-32124c46cb184d668dcca7cf3654eb83
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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