HCID 69316382, compound → HCID 86602418, compound

HRID 2373241Notes

Reaction equation

HRID 2373241 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[C:12]([CH2:13][OH:14])=[C:11]([CH:15]([CH3:17])[CH3:16])[N:10]=[C:9]3[N:18]([CH2:21][CH3:22])[N:19]=[CH:20][C:8]=23)=[CH:4][CH:3]=1>ClC(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[S:6][C:5]([C:7]2[C:12]([CH:13]=[O:14])=[C:11]([CH:15]([CH3:17])[CH3:16])[N:10]=[C:9]3[N:18]([CH2:21][CH3:22])[N:19]=[CH:20][C:8]=23)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 69316382HCID 69316382, compound

Product 1

HCID 86602418HCID 86602418, compoundYield 55.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of [4-(5-chloro-2-thienyl)-1-ethyl-6-isopropyl-1H-pyrazolo[3,4-b]pyridin-5-yl]methanol (2.526 g), activated manganese dioxide (13.1 g) in tetrachloromethane (50 ml) was refluxed for 12 hours. Another activated manganese dioxide (26.1 g) was added and the mixture was refluxed for 10 hours. After cooling, the mixture was filtered through celite and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a mixture of EtOAc and n-hexane (1:20) to give 4-(5-chloro-2-thienyl)-1-ethyl-6-isopropyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde (1.4 g) as a yellow crystal.

Workup

  1. temperaturewas refluxed for 12 hours
  2. temperaturethe mixture was refluxed for 10 hours
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered through celite
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with a mixture of EtOAc and n-hexane (1:20)

Sources & evidence

ORD record
ord-599a7d0113e343c993d00920c992923b
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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