Hydrochloric Acid → Ethyl 2-(2-methylimidazo[4,5-c]pyrid-1-yl)pyrid-5-oylacetate

HRID 892782Notes

Reaction equation

HRID 892782 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][C:3]([OH:5])=O.[CH2:8]([K])[CH3:9].C([Mg]Cl)(C)C.[CH3:16][C:17]1[N:18]([C:26]2[N:31]=[CH:30][C:29](C(Cl)=O)=[CH:28][CH:27]=2)[C:19]2[CH:24]=[CH:23][N:22]=[CH:21][C:20]=2[N:25]=1.Cl.C(=O)(O)[O-].[Na+]>O1CCCC1.ClCCl>[CH3:16][C:17]1[N:18]([C:26]2[CH:27]=[CH:28][C:29]([C:3]([CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6])=[O:5])=[CH:30][N:31]=2)[C:19]2[CH:24]=[CH:23][N:22]=[CH:21][C:20]=2[N:25]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 198771756-(2-Methylimidazo[4,5-c]pyrid-1-yl)pyrid-3-oyl chlorideHCID 178418918HCID 178418918, compoundHCID 178461627HCID 178461627, compound

Product 1

HCID 54245582Ethyl 2-(2-methylimidazo[4,5-c]pyrid-1-yl)pyrid-5-oylacetateYield 63%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl potassium malonate (57 mg) was suspended in dry tetrahydrofuran (1 ml) and 2M isopropyl magnesium chloride in THF (170 μl) added. The suspension was sonicated for 1/2 hour giving a homogeneous solution. This was added with stirring to the suspension of 6-(2-methylimidazo[4,5-c]pyrid-1-yl)pyrid-3-oyl chloride in dichloromethane. The mixture was stirred at room temperature for 1/2 hour. It was then poured into 1N hydrochloric acid, stirred for 15 minutes and adjusted to pH8 with saturated sodium bicarbonate. The aqueous phase was extracted with dichloromethane (2×10 ml), the extracts combined, dried over magnesium sulphate and the solvent removed under reduced pressure yielding the title compound as a pale red oil (40 mg, 63%) [as a 1:1 mixture of enol and keto tautomers].

Workup

  1. customThe suspension was sonicated for 1/2 hour
  2. customgiving a homogeneous solution
  3. additionThis was added
  4. stirringstirred for 15 minutes
  5. extractionThe aqueous phase was extracted with dichloromethane (2×10 ml)
  6. dry with materialdried over magnesium sulphate
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-6ce1b905a9144d07b9b8afe97677137b
Source dataset
uspto-grants-1992_06
Patent number
US05120747

Reaction notes

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