Potassium Carbonate → HCID 136183851, compound

HRID 1382895Notes

Reaction equation

HRID 1382895 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[C:24]3[C:19](=[N:20][C:21]([CH3:25])=[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:32]([O:35][CH2:36][CH2:37]Br)(=[O:34])[CH3:33]>CN(C)C=O>[C:32]([O:35][CH2:36][CH2:37][N:18]1[C:19]2=[N:20][C:21]([CH3:25])=[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:34])[CH3:33]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 178422576HCID 178422576, compound

Product 1

HCID 136183851HCID 136183851, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 6.8 g of the compound of Example 2 in 50 ml of dimethylformamide are added 4.1 g of potassium carbonate and 5 g of 2-bromoethyl acetate, and the mixture is stirred at 60° C. for 16.5 hours. The reaction mixture is poured into ice-cold water, and the precipitate is extracted with ethyl acetate. The extract is washed with water, dried and concentrated, and then the residue is recrystallized from hexane to give 5.9 g of 1-(2-acetoxyethyl)-3-(3,5-di-tertiary butyl-4-hydroxyphenyl)-6-methyl-1H-pyrazolo[-3,4-b]pyridine as pale yellowish green crystals, melting at 101.5°-103° C.

Workup

  1. additionThe reaction 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 residue is recrystallized from hexane

Sources & evidence

ORD record
ord-537a4f0a1be44127a417dc1ebdc14dba
Source dataset
uspto-grants-1989_02
Patent number
US04808620

Reaction notes

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