Sodium Hydroxide → HCID 178490916, compound

HRID 1943888Notes

Reaction equation

HRID 1943888 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([OH:11])=[N:9][NH:8][C:5]2=[N:6][CH:7]=1.Cl[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1.[OH-].[Na+]>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([OH:11])=[N:9][N:8]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 699934-Methyloxybenzyl chlorideHCID 1785189625-bromo-1H,2H,3H-pyrazolo[3,4-b]pyridin-3-one

Product 1

HCID 178490916HCID 178490916, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-Bromo-1H-pyrazolo[3,4-b]pyridin-3-ol (8.68 g, 40.56 mmol) and 1-(chloromethyl)-4-methoxybenzene (16.50 mL, 121.7 mmol) were dissolved in DMSO (250 mL). Powdered NaOH (2.433 g, 60.84 mmol) was added, and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was partitioned between EtOAc and water and separated. The aqueous layer was extracted with EtOAc (3×). The combined organic layers were washed with water (3×), saturated aqueous NaHCO3 (3×), brine, and dried over Na2SO4 and concentrated giving an oily solid. This solid was triturated with EtOAc and dried to provide 5-bromo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-3-ol (7.0 g, 51.7%) as a solid.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. customseparated
  3. extractionThe aqueous layer was extracted with EtOAc (3×)
  4. washThe combined organic layers were washed with water (3×), saturated aqueous NaHCO3 (3×), brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customgiving an oily solid
  8. customThis solid was triturated with EtOAc
  9. customdried

Sources & evidence

ORD record
ord-2beaff3a005a483e9bae2867bd3e3a7b
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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