Sodium hydride → HCID 21183034, compound

HRID 1386633Notes

Reaction equation

HRID 1386633 reaction equation
[CH2:1]([O:3][C:4]([CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5])[CH3:2].[H-].[Na+].Br[CH:20]([CH3:35])[C:21]([C:23]1[C:24]([CH:32]([CH3:34])[CH3:33])=[N:25][N:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=12)=[O:22].[Cl-].[NH4+]>O.CN(C=O)C>[CH2:15]([O:14][C:12]([C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])([CH:20]([CH3:35])[C:21]([C:23]1[C:24]([CH:32]([CH3:34])[CH3:33])=[N:25][N:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=12)=[O:22])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:13])[CH3:16]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 80471Triethyl methanetricarboxylateHCID 11770875HCID 11770875, compound

Product 1

HCID 21183034HCID 21183034, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Triethoxycarbonylmethane (1.53 g) was dissolved into DMF (20 ml), and, after adding sodium hydride (0.28 g), the mixture was stirred for 0.5 hours at room temperature. 3-(2-Bromo-propionyl)-2-isopropylpyrazolo[1,5-a]pyridine (1.77 g) was added and the mixture was stirred for 1 hour at room temperature, and then further stirred for 7 hours by heating to 80 to 100° C. Saturated aqueous solution of ammonium chloride was added to the reaction liquor, which was diluted with water, then 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 and the residue was purified by means of silica gel column chromatography (developing solvent, ethyl acetate:n-hexane=1:2) to obtain aimed product (0.67 g) as a yellow oily product.

Workup

  1. stirringthe mixture was stirred for 1 hour at room temperature
  2. stirringfurther stirred for 7 hours
  3. temperatureby heating to 80 to 100° C
  4. extractionextracted with ether
  5. washAfter the organic layer was washed with water and with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate, solvent
  7. distillationwas distilled off under reduced pressure
  8. customthe residue was purified by means of silica gel column chromatography (developing solvent, ethyl acetate:n-hexane=1:2)

Sources & evidence

ORD record
ord-a4a9dd2880374eab85cbbe13517ae9aa
Source dataset
uspto-grants-2001_07
Patent number
US06265577B1

Reaction notes

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