Dimethylformamide → 3-(1-Methyl-3-methoxycarbonyl-2-oxo-1,2-dihydropyridin-5-yl)-2-phenylpyrazolo[1,5-a]pyridine

HRID 703996Notes

Reaction equation

HRID 703996 reaction equation
[C:1]([C:4]1C(=O)NC=[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]=1)([OH:3])=[O:2].[OH-].[K+].[CH3:28]I.[CH3:30][N:31]([CH3:34])[CH:32]=[O:33]>O>[CH3:30][N:31]1[CH:34]=[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]([C:1]([O:3][CH3:28])=[O:2])[C:32]1=[O:33]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 151581293-(3-Carboxy-2-oxo-1,2-dihydropyridin-5-yl)-2-phenylpyrazolo[1,5-a]pyridine

Product 1

HCID 151581623-(1-Methyl-3-methoxycarbonyl-2-oxo-1,2-dihydropyridin-5-yl)-2-phenylpyrazolo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

To a mixture of 3-(3-carboxy-2-oxo-1,2-dihydropyridin-5-yl)-2-phenylpyrazolo[1,5-a]pyridine (0.92 g) and potassium hydroxide powder (0.54 g) in N,N-dimethylformamide (9 ml) was added 93% methyl iodide (0.64 ml) under ice-cooling (0-5° C.) The mixture was stirred for 3 hours under ice-cooling, and then at room temperature for 1 hour and diluted with water. The resultant precipitates were filtered off and the filtrate was acidified with 5% hydrochloric acid and extracted with ethyl acetate (20 ml). The extract was washed with water (5 ml) and sodium chloride aqueous solution (5 ml), then dried over magnesium sulfate. The solvent was removed and the residue was chromatographed on silica gel (12 g) with a mixture of chloroform and methanol (100:1) as an eluent. The fractions containing the object compound were combined and evaporated in vacuo to give 3-(1-methyl-3-methoxycarbonyl-2-oxo-1,2-dihydropyridin-5-yl)-2-phenylpyrazolo[1,5-a]pyridine (0.34 g).

Workup

  1. temperaturecooling
  2. waitat room temperature for 1 hour
  3. customThe resultant precipitates
  4. filtrationwere filtered off
  5. extractionextracted with ethyl acetate (20 ml)
  6. washThe extract was washed with water (5 ml) and sodium chloride aqueous solution (5 ml)
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed
  9. customthe residue was chromatographed on silica gel (12 g) with a mixture of chloroform and methanol (100:1) as an eluent
  10. additionThe fractions containing the object compound
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-52f070dffdac4c96ad6baffcdca5940f
Source dataset
uspto-grants-1991_01
Patent number
US04985444

Reaction notes

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