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Potassium Carbonate → 2-(3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-1H-pyrazolo(3,4-b)pyridin-1-yl)ethyl acetate

HRID 1382891
Notes
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Reaction equation

HRID 1382891 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[NH:18][N:17]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:31]([O:34][CH2:35][CH2:36]Br)(=[O:33])[CH3:32]>CN(C)C=O>[C:31]([O:34][CH2:35][CH2:36][N:18]1[C:19]2=[N:20][CH:21]=[CH:22][CH:23]=[C:24]2[C:16]([C:7]2[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]([OH:11])=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH:6]=2)=[N:17]1)(=[O:33])[CH3:32]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 178440702HCID 178440702, compound

Product 1

HCID 1972492-(3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-1H-pyrazolo(3,4-b)pyridin-1-yl)ethyl acetateYield 84.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 40 g of 3-(3,5-di-tertiary butyl-4-hydroxyphenyl)-1H-pyrazolo[3,4-b]pyridine in 300 ml of dimethylformamide are added 34,2 g of potassium carbonate and 31 g of 2-acetoxyethyl bromide, and the mixture is stirred at 60° C. for 11 hours. The resulting mixture is poured into ice-cold water and the precipitate is extracted with ethyl acetate and then the extract is washed with water, dried and concentrated. The resulting residue is recrystallized from isopropyl alcohol to give 43 g of 1-(2-acetoxyethyl)-3-(3,5-di-tertiary butyl-4-hydroxyphenyl)-1H-pyrazolo[3,4-b]pyridine as white crystals, melting at 115°-116° C.

Workup

  1. additionThe resulting mixture is poured into ice-cold water
  2. extractionthe precipitate is extracted with ethyl acetate
  3. washthe extract is washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe resulting residue is recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-82f14d89fef048f9aa4d9cdc1b34b7da
Source dataset
uspto-grants-1989_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04808620

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes