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

HRID 563401Notes

Reaction equation

HRID 563401 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)+=317.

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-bcea45c66af94547b6811990107d502f
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Reaction notes

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