Tetraethyl methylenediphosphonate → Ethyl 5-[2-(diethoxyphosphinyl)-E-ethenyl]imidazo[1,2-a]pyridine-2-carboxylate

HRID 861999Notes

Reaction equation

HRID 861999 reaction equation
[CH2:1]([P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])P(=O)(OCC)OCC.[H-].[Na+].[CH:20]([C:22]1[N:27]2[CH:28]=[C:29]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[N:30]=[C:26]2[CH:25]=[CH:24][CH:23]=1)=O>C1C=CC=CC=1.C(Cl)(Cl)Cl.O>[CH2:15]([O:14][P:10]([O:11][CH2:12][CH3:13])(/[CH:1]=[CH:20]/[C:22]1[N:27]2[CH:28]=[C:29]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[N:30]=[C:26]2[CH:25]=[CH:24][CH:23]=1)=[O:17])[CH3:16]

Participants

6

Reactant 3

HCID 15455Tetraethyl methylenediphosphonateHCID 24758Sodium hydrideHCID 19701256Ethyl 5-formylimidazo[1,2-a]pyridine-2-carboxylate

Product 1

HCID 19701129Ethyl 5-[2-(diethoxyphosphinyl)-E-ethenyl]imidazo[1,2-a]pyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent3×HCID 22418719Chloroform waterSolvent

Procedure

Tetraethyl methylenediphosphonate (Lancaster) in benzene was added to a benzene solution of sodium hydride (NaH). The product from Example 54, also dissolved in benzene, was then added dropwise to the reaction mixture. After stirring the resulting mixture for 2 h under an Ar atmosphere, the reaction was diluted with CHCl3 /H2O (2/1). The CHCl3 layer was separated and the aqueous layer extracted with CHCl3. Chromatography of the residue after removal of all solvent from the combined extracts gave the title product.

Workup

  1. additionwas then added dropwise to the reaction mixture
  2. customThe CHCl3 layer was separated
  3. extractionthe aqueous layer extracted with CHCl3
  4. customChromatography of the residue after removal of all solvent from the combined extracts

Sources & evidence

ORD record
ord-81a4b00d1ba54e629902819256bfa949
Source dataset
uspto-grants-1998_02
Patent number
US05716964

Reaction notes

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