2-Iodoxybenzoic acid → 5-bromo-2-methyl-2H-indazole-4-carbaldehyde

HRID 1639798Notes

Reaction equation

HRID 1639798 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH3:11])[N:7]=2)[C:3]=1[CH2:12][OH:13].I(C1C=CC=CC=1C(O)=O)(=O)=O>CS(C)=O.C(OCC)C>[Br:1][C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH3:11])[N:7]=2)[C:3]=1[CH:12]=[O:13]

Participants

5

Reactant 2

HCID 1087942-Iodoxybenzoic acidHCID 59334512(5-bromo-2-methyl-2H-indazol-4-yl)methanol

Product 1

HCID 593346385-bromo-2-methyl-2H-indazole-4-carbaldehydeYield 97.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

(5-Bromo-2-methyl-2H-indazol-4-yl)methanol (324 mg, 1.34 mmol) and o-iodoxybenzoic acid (414 mg, 1.48 mmol) were dissolved in dimethyl sulfoxide (6.7 mL), and the mixture was stirred at room temperature for 1 hr. The reaction solution was diluted with diethyl ether, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound (311 mg, yield 97%).

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-12f8b4e96ab1439c8586a0539c17bfce
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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