Triacetoxyperiodinane → (1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methanone

HRID 218158Notes

Reaction equation

HRID 218158 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[OH:18])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[O:18])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 59251034(1-(4-Fluorophenyl)-1H-indazol-5-yl)(phenyl)methanol

Product 1

HCID 67005723(1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methanoneYield 100.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1-(4-Fluorophenyl)-1H-indazol-5-yl)(phenyl)methanol (Example 1(f)) (2.4 g, 7.54 mmol) was dissolved in 50 mL of DCM and treated with Dess Martin periodinane (3.2 g, 7.54 mmol) and stirred overnight. The next day, the reaction was extracted from 2 M NaOH with DCM (vigorous shaking)×3, dried over MgSO4, filtered, and concentrated in vacuo. The crude material was filtered through a silica gel pad using EtOAc and concentrated to give (1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methanone (2.4 g, 100%). MS found: (M+H)+=340.

Workup

  1. extractionThe next day, the reaction was extracted from 2 M NaOH with DCM (vigorous shaking)×3
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. filtrationThe crude material was filtered through a silica gel pad
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e352caac2abf4c9ca248f79b087882b6
Source dataset
uspto-grants-2012_06
Patent number
US08198311B2

Reaction notes

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