Sodium Chloride → 3-[1-(2-Methoxycarbonylethyl)-2-oxo-1,2,5,6-tetrahydropyridin-4-yl]-2-phenylpyrazolo[1,5-a]pyridine

HRID 703978Notes

Reaction equation

HRID 703978 reaction equation
[H-].[Na+].[O:3]=[C:4]1[CH:9]=[C:8]([C:10]2[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:12][N:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=23)[CH2:7][CH2:6][NH:5]1.[C:25]([O:29][CH3:30])(=[O:28])[CH:26]=[CH2:27].[Cl-].[Na+]>O1CCCC1>[CH3:30][O:29][C:25]([CH2:26][CH2:27][N:5]1[CH2:6][CH2:7][C:8]([C:10]2[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:12][N:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=23)=[CH:9][C:4]1=[O:3])=[O:28]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 7294Methyl AcrylateHCID 24758Sodium hydrideHCID 151581103-(2-Oxo-1,2,5,6-tetrahydropyridin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine

Product 1

HCID 151581253-[1-(2-Methoxycarbonylethyl)-2-oxo-1,2,5,6-tetrahydropyridin-4-yl]-2-phenylpyrazolo[1,5-a]pyridineYield 77.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60%, 43.6 mg) was added to a mixture of 3-(2-oxo-1,2,5,6-tetrahydropyridin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine (210 mg), methyl acrylate (93.8 mg) and tetrahydrofuran (2.1 ml) under ice-cooling. The reaction mixture was stirred at room temperature for 1.5 hours. A saturated solution of sodium chloride (20 ml) was added to the reaction mixture and extracted with ethyl acetate (20 ml×2). The combined extract was washed with a saturated solution of sodium chloride (20 ml), dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel using a mixture of chloroform and ethyl acetate (10:1) to give 3-[1-[2-methoxycarbonylethyl)-2-oxo-1,2,5,6-tetrahydropyridin-4-yl]-2-phenylpyrazolo[1,5-a]pyridine (210.7 mg) as an oil.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate (20 ml×2)
  3. extractionThe combined extract
  4. washwas washed with a saturated solution of sodium chloride (20 ml)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel using
  8. additiona mixture of chloroform and ethyl acetate (10:1)

Sources & evidence

ORD record
ord-3965dab98bea4bddbbfda7cbc88ab4cc
Source dataset
uspto-grants-1991_01
Patent number
US04985444

Reaction notes

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