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Acetic Anhydride → 1-(2-acetoxyethyl)-3-(3,5-di-tertiary butylphenyl)-1H-pyrazolo[3,4-b]pyridine

HRID 1382893
Notes
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Reaction equation

HRID 1382893 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)[N:18]([CH2:25][CH2:26][OH:27])[N:17]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1O)([CH3:4])([CH3:3])[CH3:2].[C:28](OC(=O)C)(=[O:30])[CH3:29]>C1(C)C=CC=CC=1>[C:28]([O:27][CH2:26][CH2:25][N:18]1[C:19]2=[N:20][CH:21]=[CH:22][CH:23]=[C:24]2[C:16]([C:7]2[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=[C:9]([C:12]([CH3:14])([CH3:13])[CH3:15])[CH:8]=2)=[N:17]1)(=[O:30])[CH3:29]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 30873781H-Pyrazolo(3,4-b)pyridine-1-ethanol, 3-(3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl)-

Product 1

HCID 212736381-(2-acetoxyethyl)-3-(3,5-di-tertiary butylphenyl)-1H-pyrazolo[3,4-b]pyridineYield 86.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 40 g of the compound of Example 43 in 320 ml of toluene is added 22 g of acetic anhydride under stirring, and refluxed for 8 hours. After completion of the reaction, the reaction mixture is cooled to 20° C., washed with 300 ml of water twice and dried over anhydrous sodium sulfate. The toluene is concentrated and the residue is recrystallized from ethanol and dried to give 37 g of 1-(2-acetoxyethyl)-3-(3,5-di-tertiary butylphenyl)-1H-pyrazolo[3,4-b]pyridine, melting at 115°-116° C.

Workup

  1. temperaturerefluxed for 8 hours
  2. customAfter completion of the reaction
  3. washwashed with 300 ml of water twice
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe toluene is concentrated
  6. customthe residue is recrystallized from ethanol
  7. customdried

Sources & evidence

ORD record
ord-3db335a915d04e1c83ac3dd8cedd4b8c
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