Triacetoxyperiodinane → 1-(4-fluorophenyl)-1H-indazole-5-carbaldehyde

HRID 218123Notes

Reaction equation

HRID 218123 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]([CH2:17][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]([CH:17]=[O:18])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67005185(1-(4-Fluorophenyl)-1H-indazol-5-yl)methanol

Product 1

HCID 579436121-(4-fluorophenyl)-1H-indazole-5-carbaldehydeYield 100.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1-(4-Fluorophenyl)-1H-indazol-5-yl)methanol (2.46 g, 10.2 mmol) was dissolved in 80 mL DCM and treated with commercially available Dess-Martin periodinane (4.3 g, 10.2 mmol). The reaction was complete in 2 h and was filtered through a plug of SiO2 using DCM/hexane (3:1) and concentrated to give 2.47 g (100%) of 1-(4-fluorophenyl)-1H-indazol-5-carboxaldehyde. MS found: (M+H)+=241.

Workup

  1. filtrationwas filtered through a plug of SiO2
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a55a7561b9f847c2a6204666b886d21c
Source dataset
uspto-grants-2012_06
Patent number
US08198311B2

Reaction notes

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