Potassium Carbonate → HCID 86602964, compound

HRID 2067929Notes

Reaction equation

HRID 2067929 reaction equation
COP(=O)OC.[C:7](=O)([O-])[O-].[K+].[K+].[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[N:21]1[C:25]([CH3:26])=[C:24]([CH:27]=O)[N:23]=[C:22]1[CH3:29]>CO>[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[N:21]1[C:25]([CH3:26])=[C:24]([C:27]#[CH:7])[N:23]=[C:22]1[CH3:29]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13361Phosphonic acid, dimethyl esterHCID 86602963HCID 86602963, compound

Product 1

HCID 86602964HCID 86602964, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Diazo-2-oxo-propyl)-phosphonic acid dimethyl ester (0.37 g, 2 mmol) was dissolved in 20 mL methanol. Potassium carbonate (0.38 g, 3 mmol) was added. A solution of 1-(2,4-Difluoro-phenyl)-2,5-dimethyl-1H-imidazole-4-carbaldehyde (0.32 g, 1 mmol) in 5 ml methanol was added drop wise at room temperature. The reaction mixture was stirred at room temperature overnight. The solvent was evaporated. The residue was taken up in 15 ml water and extracted three times with ethyl acetate (15 ml each). The combined organic extracts were dried with sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel (heptane/ethyl acetate 90:10→50:50 gradient) and the desired compound was obtained as a light yellow solid (0.165 g, 52%), MS: m/e=233.1 (M+).

Workup

  1. customThe solvent was evaporated
  2. extractionextracted three times with ethyl acetate (15 ml each)
  3. dry with materialThe combined organic extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by flash chromatography on silica gel (heptane/ethyl acetate 90:10→50:50 gradient)

Sources & evidence

ORD record
ord-87820be94a3a4e99b656759ff30ce51b
Source dataset
uspto-grants-2012_10
Patent number
US08293916B2

Reaction notes

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