Phosphorus oxychloride → 4-chloro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine

HRID 2070025Notes

Reaction equation

HRID 2070025 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[C:12]3[N:13]=[CH:14][CH:15]=[C:16](O)[C:11]=3[CH:10]=[N:9]2)=[CH:5][CH:4]=1.P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:16]1[CH:15]=[CH:14][N:13]=[C:12]2[N:8]([CH2:7][C:6]3[CH:18]=[CH:19][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[N:9]=[CH:10][C:11]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178490904HCID 178490904, compound

Product 1

HCID 593985764-chloro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridineYield 70%

Conditions

Temperature
70 °C

Procedure

1-(4-Methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-ol (759 mg) was dissolved in phosphorus oxychloride (6 mL). The resulting mixture was stirred at 70° C. for 1 hour. The reaction solution was concentrated under reduced pressure. The residue was diluted with ethyl acetate and carefully washed with a sodium bicarbonate solution. The organic layer was dried (using sodium sulfate), and the drying agent was removed by filtration. The filtrate was concentrated under reduced pressure. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate=5/0 to 3/1) to give 4-chloro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine (568 mg, yield: 70%) as a colorless solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionThe residue was diluted with ethyl acetate
  3. washcarefully washed with a sodium bicarbonate solution
  4. dry with materialThe organic layer was dried (using sodium sulfate)
  5. customthe drying agent was removed by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate=5/0 to 3/1)

Sources & evidence

ORD record
ord-a7e491f730de4668afbcd81c62b6b829
Source dataset
uspto-grants-2012_10
Patent number
US08299252B2

Reaction notes

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