HCID 178520041, compound → HCID 178520040, compound

HRID 1749875Notes

Reaction equation

HRID 1749875 reaction equation
[F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[CH2:13][OH:14]>C(OCC)(=O)C.[O-2].[O-2].[Mn+4]>[F:16][C:2]([F:1])([F:15])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[CH:13]=[O:14]

Participants

4

Reactant 1

HCID 178520041HCID 178520041, compound

Product 1

HCID 178520040HCID 178520040, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of [5-(trifluoromethoxy)-1H-indazol-3-yl]methanol (0.109 g, 0.470 mmol) in ethyl acetate (2 mL) was added with manganese dioxide (0.409 g, 4.70 mmol), and the reaction mixture was stirred overnight at room temperature. The reaction mixture was filtered through Celite, then the filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol) to obtain the objective 5-(trifluoromethoxy)-1H-indazole-3-carbaldehyde (0.0710 g, 65%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-f2adfe0f2268428e867efb996a241241
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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