Potassium Carbonate → 4-Ethynyl-1-(4-fluorophenyl)-2-methyl-1H-imidazole

HRID 1009738Notes

Reaction equation

HRID 1009738 reaction equation
COP(=O)OC.[C:7](=O)([O-])[O-].[K+].[K+].[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH:24]=[C:23]([CH:25]=O)[N:22]=[C:21]2[CH3:27])=[CH:16][CH:15]=1>CO>[C:25]([C:23]1[N:22]=[C:21]([CH3:27])[N:20]([C:17]2[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=2)[CH:24]=1)#[CH:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13361Phosphonic acid, dimethyl esterHCID 859979931-(4-fluoro-phenyl)-2-methyl-1H-imidazole-4-carbaldehyde

Product 1

HCID 116655954-Ethynyl-1-(4-fluorophenyl)-2-methyl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Diazo-2-oxo-propyl)-phosphonic acid dimethyl ester (6.51 g, 33.9 mmol) was dissolved in 100 mL methanol. Potassium carbonate (7.81 g, 56.5 mmol) was added. A solution of 1-(4-fluoro-phenyl)-2-methyl-1H-imidazole-4-carbaldehyde (5.77 g, 45 mmol) in 100 mmol methanol was added dropwise at room temperature. The reaction mixture was stirred at room temperature overnight. The solvent was evaporated. The residue was taken up in 150 mL water and extracted three times with ethyl acetate (150 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 100:0->0:100 gradient) and the desired compound was obtained as a white solid (3.81 g, 67%), MS: m/e=200.1 (M+).

Workup

  1. customThe solvent was evaporated
  2. extractionextracted three times with ethyl acetate (150 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 100:0->0:100 gradient)

Sources & evidence

ORD record
ord-4dbe0aaa0fbe4db6ad9d09f714b9b6fe
Source dataset
uspto-grants-2011_07
Patent number
US07973165B2

Reaction notes

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