Ethyl bromoacetate → HCID 67210036, compound

HRID 402474Notes

Reaction equation

HRID 402474 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:8]2[NH:9][C:10](=[O:13])[CH:11]=[CH:12][C:7]=2[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:5]1.Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>CN(C=O)C>[CH3:3][N:4]1[C:8]2=[N:9][C:10]([O:13][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:11][CH:12]=[C:7]2[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:5]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 136376519HCID 136376519, compound

Product 1

HCID 67210036HCID 67210036, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (0.115 g, 2.886 mmol) was added to an ice cold solution of 1-methyl-3-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (0.325 g, 1.443 mmol) in DMF (5.0 mL) and stirred at ambient temperature for 30 min. Ethyl bromoacetate (0.482 g, 2.886 mmol) was added to the reaction mixture dropwise and stirring was continued for 2 h. After completion of the reaction, the excess of NaH was quenched by the addition of ice cold water. Diethyl ether was added and the mixture was extracted with water and brine. The organic layer was dried over Na2SO4 and filtered. Concentration of the organic layer furnished the title compound as a white solid (0.353 g, 79%). [1H-NMR (CDCl3, 300 MHz) δ 8.2 (d, 1H), 7.94-7.87 (m, 2H), 7.54-7.36 (m, 3H), 6.79 (d, 1H), 5.0 (s, 2H), 4.29 (q, 2H), 4.05 (s, 3H), 1.30 (t, 3H); HPLC RtA=5.555 min (95%); LCMS RtC=1.967 min; [M+H]+=312.1]

Workup

  1. stirringstirring
  2. waitwas continued for 2 h
  3. customAfter completion of the reaction
  4. customthe excess of NaH was quenched by the addition of ice cold water
  5. additionDiethyl ether was added
  6. extractionthe mixture was extracted with water and brine
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered

Sources & evidence

ORD record
ord-aae1f1258fc74068bdee4f9d121ab610
Source dataset
uspto-grants-2014_06
Patent number
US08742106B2

Reaction notes

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