Potassium Hydroxide → HCID 50925481, compound

HRID 877485Notes

Reaction equation

HRID 877485 reaction equation
C(OC[N:9]1[C:17]2[C:16]([Cl:18])=[CH:15][C:14]([Cl:19])=[CH:13][C:12]=2[C:11]2[CH2:20][CH2:21][C:22]([C:28]([F:31])([F:30])[F:29])([O:23][Si](C)(C)C)[C:10]1=2)(=O)C(C)(C)C.[OH-].[K+]>C1COCC1.O>[Cl:18][C:16]1[C:17]2[NH:9][C:10]3[C:22]([C:28]([F:31])([F:29])[F:30])([OH:23])[CH2:21][CH2:20][C:11]=3[C:12]=2[CH:13]=[C:14]([Cl:19])[CH:15]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67377715HCID 67377715, compound

Product 1

HCID 50925481HCID 50925481, compoundYield 430%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To (5,7-Dichloro-3-(trifluoromethyl)-3-(trimethylsilyloxy)-2,3-dihydrocyclopenta[b]indole-4(1H)-yl)methyl pivalate (0.32 g, 0.6 mmol) in THF (6.0 mL), cooled to 0° C., KOH (0.18 g, 3.2 mmol), in H2O (6.0 mL) was added. The reaction mixture was slowly warmed to room temperature and stirred for 16 h, diluted with water (10 mL) and extracted with CH2Cl2 (3×10 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to give the crude compound which was purified by silica gel chromatography [EtOAc-hexane (3:17) as eluant] to afford the title compound as a white solid (0.80 g, 40%). 1H NMR (500 MHz, DMSO-d6, δ in ppm) 11.75 (s, 1H), 7.55 (s, 1H), 7.30 (d, 1.5 Hz, 1H), 6.83 (s, 1H), 2.93-2.88 (m, 2H), 2.78-2.74 (m, 1H), 2.53-2.50 (m, 1H).

Workup

  1. extractionextracted with CH2Cl2 (3×10 mL)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customto give the crude compound which
  5. customwas purified by silica gel chromatography [EtOAc-hexane (3:17) as eluant]

Sources & evidence

ORD record
ord-458b19f89cfc4aebb66a116ff5786004
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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