Ethyl bromoacetate → HCID 14796395, compound

HRID 1084844Notes

Reaction equation

HRID 1084844 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:9]=2)=[CH:4][CH:3]=1.Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:17]1([N:10]2[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:16]3[C:8]([C:5]3[CH:4]=[CH:3][C:2]([O:1][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:7][CH:6]=3)=[N:9]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 135621433HCID 135621433, compound

Product 1

HCID 14796395HCID 14796395, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

In 400 ml of dimethylformamide were suspended 39.3 g of 3-(4-hydroxyphenyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridine, 34.4 g of ethyl bromoacetate and 28.4 g of potassium carbonate. The mixture was stirred under heating at 70° C. for 2 hours. The reaction mixture was concentrated under reduced pressure and the residue was extracted with benzene-water. The organic layer was concentrated. Hexane was added to the residue for crystallization. The obtained crude crystals were recrystallized from isopropyl ether to give 28 g of ethyl 4-(1-phenyl-1H-pyrazolo[3,4-b]pyridin-3-yl)phenoxyacetate, m.p. 118°-120° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionthe residue was extracted with benzene-water
  3. concentrationThe organic layer was concentrated
  4. additionHexane was added to the residue for crystallization
  5. customThe obtained crude crystals
  6. customwere recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-4ce9d7e6fe4d465093681353bdafbe86
Source dataset
uspto-grants-1991_04
Patent number
US05006520

Reaction notes

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