Triacetoxyperiodinane → HCID 22676761, compound

HRID 1006292Notes

Reaction equation

HRID 1006292 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[F:23][C:24]([F:56])([F:55])[CH:25]([C:27]1[N:28]([CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([C:51]([F:54])([F:53])[F:52])[CH:46]=2)[C:29]2[C:34]([C:35]=1[C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=1)=[CH:33][CH:32]=[CH:31][CH:30]=2)[OH:26]>ClCCl>[F:56][C:24]([F:23])([F:55])[C:25]([C:27]1[N:28]([CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([C:51]([F:54])([F:53])[F:52])[CH:46]=2)[C:29]2[C:34]([C:35]=1[C:36]1[CH:37]=[CH:38][C:39]([O:42][CH3:43])=[CH:40][CH:41]=1)=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 22676779HCID 22676779, compound

Product 1

HCID 22676761HCID 22676761, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin reagent (39 mg, 0.09 mmol) was added to a stirred solution of 2,2,2-trifluoro-1-(3-(4-methoxphenyl)-1-{[3-(trifluoromethyl)phenyl]methyl}indol-2-yl)ethan-1-ol (Example 219, 40 mg, 0.08 mmol) in dichloromethane (2 mL). The resulting solution was stirred for 2 hours, more oxidant was added, and then the mixture was left stirring for 18 h. The reaction was quenched with a mixed aqueous solution of saturated sodium bicarbonate and saturated sodium thio sulfate (1:1, 10 mL), and the mixture was extracted with ethyl acetate (2×10 mL). The combined organic extracts were washed with water, and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. Silica gel flash chromatography using hexane/ethyl acetate (4/1) as the eluant gave 2,2,2-trifluoro-1-(3-(4-methoxyphenyl)-1-{[3-(trifluoromethyl)phenyl]methyl}indol-2-yl)ethan-1-one as an orange oil (27 mg, 70%): 1H NMR (300 MHz, DMSO-d6) δ 7.76 (d, 1H), 7.47-7.62 (m, 4H), 7.20-7.45 (m, 5H), 7.05 (d, 2H), 5.76 (s, 2H); MS (MH+) calcd for C25H18F6NO2: 478., found: 478.

Workup

  1. additionmore oxidant was added
  2. waitthe mixture was left
  3. stirringstirring for 18 h
  4. customThe reaction was quenched with a mixed aqueous solution of saturated sodium bicarbonate and saturated sodium thio sulfate (1:1, 10 mL)
  5. extractionthe mixture was extracted with ethyl acetate (2×10 mL)
  6. washThe combined organic extracts were washed with water, and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-02b0891f0ecc4a1e85b85347fb2eec62
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

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