Diethyl Malonate → HCID 21183031, compound

HRID 1386634Notes

Reaction equation

HRID 1386634 reaction equation
[Na].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].Br[CH2:14][C:15]([C:17]1[C:18]([CH:26]([CH3:28])[CH3:27])=[N:19][N:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=12)=[O:16]>C(O)C>[CH2:11]([O:10][C:2]([CH:3]([CH2:14][C:15]([C:17]1[C:18]([CH:26]([CH3:28])[CH3:27])=[N:19][N:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=12)=[O:16])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:9])[CH3:12]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 5360545SodiumHCID 21183036HCID 21183036, compound

Product 1

HCID 21183031HCID 21183031, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

Sodium (0.10 g) was dissolved into ethanol (4 ml) and diethyl malonate (0.71 g) was added at room temperature. After stirring for 20 minutes at 50° C., a solution of 3-(2-bromoacetyl)-2-isopropylpyrazolo[1,5-a]pyridine (1.06 g) in ethanol (6 ml) was added and the mixture was stirred for 75 minutes at 80° C. The reaction liquor was concentrated, and, water and ethyl acetate were added to the residue to separate the organic layer. After the organic layer was washed with water and with saturated brine and dried over anhydrous sodium sulfate, solvent was distilled off and the residue was purified by means of silica gel column chromatography (developing solvent, ethyl acetate, n-hexane=1:3) to obtain aimed product (0.44 g) as pale yellow powder.

Workup

  1. additionwas added at room temperature
  2. stirringthe mixture was stirred for 75 minutes at 80° C
  3. concentrationThe reaction liquor was concentrated
  4. additionwater and ethyl acetate were added to the residue
  5. customto separate the organic layer
  6. washAfter the organic layer was washed with water and with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate, solvent
  8. distillationwas distilled off
  9. customthe residue was purified by means of silica gel column chromatography (developing solvent, ethyl acetate, n-hexane=1:3)

Sources & evidence

ORD record
ord-8efaf6a4556c4532bbf92cd56fca445e
Source dataset
uspto-grants-2001_07
Patent number
US06265577B1

Reaction notes

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