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

HRID 1382892Notes

Reaction equation

HRID 1382892 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]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:35](Cl)(=[O:37])[CH3:36]>C(Cl)(Cl)Cl>[C:35]([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: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:37])[CH3:36]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 30873781H-Pyrazolo(3,4-b)pyridine-1-ethanol, 3-(3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl)-

Product 1

HCID 1972492-(3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-1H-pyrazolo(3,4-b)pyridin-1-yl)ethyl acetateYield 86.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5.2 g of the compound of Example 43 in 30 ml of chloroform is added 2.1 g of triethylamine, and the mixture is cooled and then stirred. To the reaction mixture is added dropwise 1.7 g of acetyl chloride below 0° C. over 5 minutes. After completion of the addition, the mixture is stirred at room temperature for 3 hours, and the reaction solution is washed with water, dried and concentrated. The residue is recrystallized from isopropyl alcohol to give 5 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. temperaturethe mixture is cooled
  2. additionAfter completion of the addition
  3. stirringthe mixture is stirred at room temperature for 3 hours
  4. washthe reaction solution is washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue is recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-a11d603303a94e34b7be66758e703af1
Source dataset
uspto-grants-1989_02
Patent number
US04808620

Reaction notes

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