Pyridine → HCID 86602410, compound

HRID 2373228Notes

Reaction equation

HRID 2373228 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([CH:14]=O)=[C:12]([CH3:16])[N:11]=[C:10]3[N:17]([CH2:20][CH3:21])[N:18]=[CH:19][C:9]=23)[CH:5]=[N:6][CH:7]=1.N1C=CC=CC=1.Cl.[NH2:29][OH:30]>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([CH:14]=[N:29][OH:30])=[C:12]([CH3:16])[N:11]=[C:10]3[N:17]([CH2:20][CH3:21])[N:18]=[CH:19][C:9]=23)[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 86602411HCID 86602411, compound

Product 1

HCID 86602410HCID 86602410, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(5-bromo-3-pyridyl)-1-ethyl-6-methyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde (34 mg) in DMF (1 ml) was added pyridine (0.032 ml) and hydroxylamine hydrochloride (13.7 mg) at room temperature and the mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was washed with water, brine, dried over anhydrous MgSO4 and concentrated in vacuo to give 4-(5-bromo-3-pyridyl)-1-ethyl-6-methyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde oxime (35 mg) as a yellow crystal.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5fb2fc7b96ad4c35a64df854c88f53b5
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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