Sodium Acetate → HCID 86602402, compound

HRID 2373219Notes

Reaction equation

HRID 2373219 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:13]([CH2:14][OH:15])=[C:12]([CH3:16])[N:11]=[C:10]3[N:17]([CH2:20][CH3:21])[N:18]=[CH:19][C:9]=23)[CH:5]=[CH:4][N:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C([O-])(=O)C.[Na+]>C(Cl)Cl.C(OCC)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:13]([CH:14]=[O:15])=[C:12]([CH3:16])[N:11]=[C:10]3[N:17]([CH2:20][CH3:21])[N:18]=[CH:19][C:9]=23)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 86602403HCID 86602403, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 86602402HCID 86602402, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of [4-(2-chloro-4-pyridyl)-1-ethyl-6-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl]methanol (30 mg), pyridinium chlorochromate (34.2 mg), sodium acetate (5.7 mg) in DCM (2 ml) was stirred at room temperature for 2 hours. The reaction mixture was diluted with diethylether and filtrated through celite pad. After evaporation of filtrate, the residue was purified by flash column chromatography on silica gel eluting with a mixture of EtOAc and n-hexane (1:4) to give 4-(2-chloro-4-pyridyl)-1-ethyl-6-methyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde (29 mg) as a white crystal.

Workup

  1. filtrationfiltrated through celite pad
  2. customAfter evaporation of filtrate
  3. customthe residue was purified by flash column chromatography on silica gel eluting with a mixture of EtOAc and n-hexane (1:4)

Sources & evidence

ORD record
ord-a874def354ab4a3983f50ef781039e6e
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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