Potassium Hydroxide → HCID 52942229, compound

HRID 877476Notes

Reaction equation

HRID 877476 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([F:24])[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)[CH2:10][CH2:9][CH2:8][C:7]2=1.[OH-].[K+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([F:24])[CH:5]=[C:6]2[C:14]=1[NH:13][C:12]1[C:11]([C:20]([F:23])([F:21])[F:22])([OH:15])[CH2:10][CH2:9][CH2:8][C:7]2=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67377828HCID 67377828, compound

Product 1

HCID 52942229HCID 52942229, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

8-Chloro-6-fluoro-1-(trifluoromethyl)-1-(trimethylsilyloxy)-2,3,4,9-tetrahydro-1H-carbazole (0.1 g, 0.26 mmol) was dissolved in THF (10 mL) and KOH (0.073 g, 1.3 mmol), in 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 to give the crude compound which was purified by silica gel chromatography [EtOAc-hexane (1:4) as eluant] to provide the title compound (0.02 g, 24%) (HPLC 96%). 1H NMR (500 MHz, CDCl3, δ in ppm) 8.27 (bs, 1H), 7.12-7.11 (d, J=9.0 Hz, 1H), 7.08-7.0 (d, J=8.5 Hz, 1H), 2.82-2.77 (m, 1H), 2.71-2.65 (m, 1H), 2.49 (s, 1H), 2.29-2.23 (m, 1H), 2.12-2.09 (m, 1H), 2.05-2.02 (m, 2H).

Workup

  1. extractionextracted with EtOAc (2×25 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 silica gel chromatography [EtOAc-hexane (1:4) as eluant]

Sources & evidence

ORD record
ord-406eab1c0b8c4035a43faad4557acca8
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

Loading…