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

HRID 860147Notes

Reaction equation

HRID 860147 reaction equation
COP([C:7](=[N+:11]=[N-])[C:8](=O)[CH3:9])(=O)OC.C(=O)([O-])[O-].[K+].[K+].[F:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH:30]=C(C=O)N=[C:27]2[CH3:33])=[CH:22][CH:21]=1>CO>[C:8]([C:7]1[N:11]=[C:27]([CH3:33])[N:26]([C:23]2[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=2)[CH:30]=1)#[CH:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 859979931-(4-fluoro-phenyl)-2-methyl-1H-imidazole-4-carbaldehydeHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

(1-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 RT. The reaction mixture was stirred at RT 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+). 1-(3,4-Dichloro-phenyl)-4-ethynyl-2-methyl-1H-imidazole (IV-2) [MS: m/e=252.1 (M+)] was prepared in accordance with the method of example IV-1 from 3,4-dichloroaniline.

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-b13c84298a1147c58efc190db3b218c6
Source dataset
uspto-grants-2006_12
Patent number
US07153874B2

Reaction notes

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