Triethylamine → 3-(3,5-di-tertiary butyl-4-hydroxyphenyl)-1-(2-ethoxycarbonyloxyethyl)-1H-pyrazolo[3,4-b]-pyridine

HRID 1382894Notes

Reaction equation

HRID 1382894 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:39])[O:36][CH2:37][CH3:38]>C(Cl)(Cl)Cl>[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][O:27][C:35]([O:36][CH2:37][CH3:38])=[O:39])[N:17]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 30873781H-Pyrazolo(3,4-b)pyridine-1-ethanol, 3-(3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl)-

Product 1

HCID 1361715643-(3,5-di-tertiary butyl-4-hydroxyphenyl)-1-(2-ethoxycarbonyloxyethyl)-1H-pyrazolo[3,4-b]-pyridineYield 85.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3.7 g of the compound of Example 43 in 20 ml of chloroform is added 1.5 g of triethylamine, and to the mixture with stirring at -10°--2° C. is added 1.4 g of ethyl chlorocarbonate dropwise. After completion of the addition, the whole mixture is stirred at 0° C. for 3 hours, and then at room temperature for 2 hours. The reaction solution is washed with water, dried and concentrated, and then the resulting residue is recrystallized from isopropyl ether to give 3.8 g of 3-(3,5-di-tertiary butyl-4-hydroxyphenyl)-1-(2-ethoxycarbonyloxyethyl)-1H-pyrazolo[3,4-b]-pyridine as white crystals, melting at 103°-105° C.

Workup

  1. additionAfter completion of the addition
  2. stirringthe whole mixture is stirred at 0° C. for 3 hours
  3. washThe reaction solution is washed with water
  4. customdried
  5. concentrationconcentrated
  6. customthe resulting residue is recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-2fee54b2f6b740b2a16a18e3a8a5968a
Source dataset
uspto-grants-1989_02
Patent number
US04808620

Reaction notes

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