4-Phenyl-1-butyne → ethyl 2-methyl-4-(4-phenylbut-1-ynyl)-1H-imidazole-1-carboxylate

HRID 422267Notes

Reaction equation

HRID 422267 reaction equation
I[C:2]1[N:3]=[C:4]([CH3:12])[N:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:6]=1.[C:13]1([CH2:19][CH2:20][C:21]#[CH:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(N(CC)CC)C.[Cu+2].[I-].[I-].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:12][C:4]1[N:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:6]=[C:2]([C:22]#[C:21][CH2:20][CH2:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1

Participants

6

Reactant 2

HCID 1233604-Phenyl-1-butyneHCID 66598321ethyl 4-iodo-2-methyl-1H-imidazole-1-carboxylate

Product 1

HCID 66598146ethyl 2-methyl-4-(4-phenylbut-1-ynyl)-1H-imidazole-1-carboxylateYield 70.2%

Reagents, catalysts & solvents 3

HCID 44148441CID 44148441CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent2×

Procedure

In a dry reaction tube containing in suspension iodide copper (20 mg, 0.1 mmol) and triethylamine (5.81 mL 41.40 mmol), were added ethyl 4-iodo-2-methyl-1H-imidazole-1-carboxylate (580 mg, 2.07 mmol) and the Pd(PPh3)2Cl2 (66 mg, 0.1 mmol). A yellow suspension is obtained and after a few minutes stirred at room temperature was added the commercially available 4-phenyl-1-butyn (269 mg, 2.07 mmol) in triethylamine (0.5 mL). Immediately the color of the reaction turns to black. The mixture was stirred at room temperature for 30 min and then at 80° C. for 20 h Triethylamine was concentrated under reduce pressure and the residue was dissolved in DCM. The organic layer was washed with saturated NH4Cl, water and brine, dried (MgSO4) and concentrated. Purification by flash chromatography (prepacked 25 g silicagel column, DCM/MeOH: 99/1 as eluent to afford 410 mg of ethyl 2-methyl-4-(4-phenylbut-1-ynyl)-1H-imidazole-1-carboxylate (Yield: 70%) as a brown oil.

Workup

  1. customIn a dry reaction tube
  2. customA yellow suspension is obtained and after a few minutes
  3. stirringThe mixture was stirred at room temperature for 30 min
  4. concentrationat 80° C. for 20 h Triethylamine was concentrated
  5. dissolutionthe residue was dissolved in DCM
  6. washThe organic layer was washed with saturated NH4Cl, water and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customPurification by flash chromatography (prepacked 25 g silicagel column, DCM/MeOH

Sources & evidence

ORD record
ord-afb454195ee54d559580c3970ba349e2
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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