Methyl propiolate → HCID 9964732, compound

HRID 1610840Notes

Reaction equation

HRID 1610840 reaction equation
Cl.[NH:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH2:7][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9].C(=O)([O-])O.[Na+].[C:21](OC)(=[O:24])[C:22]#[CH:23]>ClCCl.CO>[C:8]([C:7]1[CH:23]=[CH:22][C:21](=[O:24])[N:2]2[CH:6]=[CH:5][NH:4][C:3]=12)(=[O:9])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 13536Methyl propiolateHCID 516892Sodium BicarbonateHCID 222582212-(1H-Imidazol-2-yl)-1-phenylethan-1-one--hydrogen chloride (1/1)

Product 1

HCID 9964732HCID 9964732, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

500 mg (2.25 mmol) of 2-(1H-Imidazol-2-yl)-1-phenylethanone hydrochloride (example L, step 1) are suspended in dichlormethane. Sodium hydrogen carbonate is added to the suspension and stirred for 1 h at rt. The suspension is filtrated and the solvent is evaporated under vacuum to yield the free base. The crude is dissolved in 3 ml methanol. 188.78 mg (2.25 mmol) of methyl propiolate are added dropwise to the solution. The mixture is stirred for 24 h at rt. The suspension is filtrated and the precipitate is washed with methanol and diethylether to yield 214 mg (40.0% of th.) 8-Benzoylimidazo[1,2-a]pyridin-5(1H)-one.

Workup

  1. filtrationThe suspension is filtrated
  2. customthe solvent is evaporated under vacuum
  3. customto yield the free base
  4. stirringThe mixture is stirred for 24 h at rt
  5. filtrationThe suspension is filtrated
  6. washthe precipitate is washed with methanol and diethylether

Sources & evidence

ORD record
ord-c4059a2e0a4d4fc3aad7a7ca2842db2e
Source dataset
uspto-grants-2006_01
Patent number
US06984646B2

Reaction notes

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