Potassium Carbonate → HCID 54185884, compound

HRID 1029413Notes

Reaction equation

HRID 1029413 reaction equation
C(OP([CH2:9][C:10]([N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[CH2:18][CH3:19])=[O:11])(OCC)=O)C.[H-].[Na+].[N:22]1[CH:27]=[CH:26][C:25]([C:28]2[C:36]([CH:37]=O)=[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][N:30]3[N:29]=2)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[N:22]1[CH:27]=[CH:26][C:25]([C:28]2[C:36]([CH:37]=[CH:9][C:10]([N:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]3[CH2:18][CH3:19])=[O:11])=[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][N:30]3[N:29]=2)=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 19092389HCID 19092389, compoundHCID 19092436HCID 19092436, compound

Product 1

HCID 54185884HCID 54185884, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
24 °C

Procedure

A solution of 1-(2-diethoxyphosphorylacetyl)-2-ethylpiperidine (0.99 g) in tetrahydrofuran (1.8 ml) was added dropwise to a suspension of sodium hydride (60%, 0.14 g) in tetrahydrofuran (4.5 ml) at 23° to 25° C. After being stirred at 24° C. for 30 minutes, 2-(4-pyridyl)pyrazolo[1,5-a]pyridine-3-carbaldehyde (0.63 g) was added to the mixture and then stirred at room temperature for 1 hour. The reaction mixture was poured into aqueous potassium carbonate solution and extracted with ethyl acetate (×2). The combined extracts were washed with saturated sodium chloride aqueous solution, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (25 g) with a mixture of chloroform and methanol (100:1) as an eluent. The fractions containing objective compound were combined and evaporated in vacuo to give crystals. This was recrystallized from a mixture of ethanol and water (1:1) to give 1-[3-{2-(4-pyridyl)pyrazolo[1,5-a]pyridin-3-yl}acryloyl]-2-ethylpiperidine (trans isomer) (0.38 g).

Workup

  1. stirringstirred at room temperature for 1 hour
  2. extractionextracted with ethyl acetate (×2)
  3. washThe combined extracts were washed with saturated sodium chloride aqueous solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel (25 g) with a mixture of chloroform and methanol (100:1) as an eluent
  7. additionThe fractions containing objective compound
  8. customevaporated in vacuo
  9. customto give crystals
  10. customThis was recrystallized from a mixture of ethanol and water (1:1)

Sources & evidence

ORD record
ord-ec79937bae6c417ebd0f5969dfccf1e4
Source dataset
uspto-grants-1992_04
Patent number
US05102878

Reaction notes

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