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

HRID 466035Notes

Reaction equation

HRID 466035 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

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 (0°-5° C.)
  2. temperaturecooling
  3. waitat room temperature for 1 hour
  4. customThe resultant precipitates
  5. filtrationwere filtered off
  6. extractionextracted with ethyl acetate (20 ml)
  7. washThe extract was washed with water (5 ml) and sodium chloride aqueous solution (5 ml)
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was removed
  10. customthe residue was chromatographed on silica gel (12 g) with a mixture of chloroform and methanol (100:1) as an eluent
  11. additionThe fractions containing the object compound
  12. customevaporated in vacuo

Sources & evidence

ORD record
ord-ed44c8dc12994068b02a3fea6c609469
Source dataset
uspto-grants-1992_10
Patent number
US05155114

Reaction notes

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