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

HRID 447219

Reaction equation

HRID 447219 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-99961545464642ebb8da4b13f6b117db
Source dataset
uspto-grants-2013_07
Patent number
US08481548B2

Linked notes

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