Water → HCID 21183033, compound

HRID 1386631Notes

Reaction equation

HRID 1386631 reaction equation
[CH:1]([C:4]1[C:12]([CH2:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=O)=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:25][C:26]([O:28][CH3:29])=[O:27].[Cl-].[NH4+].[OH2:32]>CN(C=O)C>[CH:1]([C:4]1[C:12]([C:13](=[O:32])[CH:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:25][C:26]([O:28][CH3:29])=[O:27])=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 962WaterHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 60984Methyl bromoacetateHCID 21183035HCID 21183035, compound

Product 1

HCID 21183033HCID 21183033, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Isopropyl-3-phenacylpyrazolo[1,5-a]pyridine (1.90 g) was dissolved into DMF (30 ml), and, after adding sodium hydride (0.35 g), the mixture was stirred for 0.5 hours at room temperature. Methyl 2-bromoacetate (1.36 g) was added, and, after stirring the mixture for 3 hours at room temperature, saturated aqueous solution of ammonium chloride was added and diluted with water, which was extracted with ether. After the organic layer was washed with water and with saturated brine and dried over anhydrous sodium sulfate, solvent was distilled off under reduced pressure. The residue was purified by means of silica gel column chromatography (developing solvent, ethyl acetate:n-hexane=1:3) to obtain aimed product (1.58 g) as a yellow oily product.

Workup

  1. stirringafter stirring the mixture for 3 hours at room temperature
  2. extractionwas extracted with ether
  3. washAfter the organic layer was washed with water and with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate, solvent
  5. distillationwas distilled off under reduced pressure
  6. customThe residue was purified by means of silica gel column chromatography (developing solvent, ethyl acetate:n-hexane=1:3)

Sources & evidence

ORD record
ord-326259b0f3c44d52938f4466be084343
Source dataset
uspto-grants-2001_07
Patent number
US06265577B1

Reaction notes

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