Triacetoxyperiodinane → HCID 66618805, compound

HRID 406308Notes

Reaction equation

HRID 406308 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[N:28]=[C:12]3[CH:13]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[C:24]([F:27])([F:26])[F:25])[CH2:14][CH:15]([OH:17])[CH2:16][N:11]3[N:10]=2)[CH:6]=[CH:5][C:4]=1[N:29]1[CH:33]=[C:32]([CH3:34])[N:31]=[CH:30]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[N:28]=[C:12]3[CH:13]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[C:24]([F:27])([F:26])[F:25])[CH2:14][C:15](=[O:17])[CH2:16][N:11]3[N:10]=2)[CH:6]=[CH:5][C:4]=1[N:29]1[CH:33]=[C:32]([CH3:34])[N:31]=[CH:30]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 66629741HCID 66629741, compound

Product 1

HCID 66618805HCID 66618805, compoundYield 22.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[6-Methoxy-5-(4-methylimidazol-1-yl)pyridin-2-yl]-8-(2-trifluoromethylphenyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridin-6-ol obtained in Example 26 (125 mg) was dissolved in methylene chloride (3 mL), and Dess-Martin reagent (226 mg) was added at room temperature. After stirring for 30 minutes, the reaction solution was partitioned with a saturated sodium bicarbonate solution and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and then concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (mobile phase:ethyl acetate/heptane=0 to 100%→methanol/ethyl acetate=10%) to obtain the title compound (28 mg).

Workup

  1. customthe reaction solution was partitioned with a saturated sodium bicarbonate solution and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting crude product was purified by silica gel column chromatography (mobile phase:ethyl acetate/heptane=0 to 100%→methanol/ethyl acetate=10%)

Sources & evidence

ORD record
ord-8232c7a0c69f439d9a40ca7f63360975
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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