Potassium Carbonate → 1-(5-bromothiophen-2-yl)-2-methyl-1H-imidazole

HRID 2043384Notes

Reaction equation

HRID 2043384 reaction equation
[Br:1][C:2]1[S:3][C:4](Br)=[CH:5][CH:6]=1.[CH3:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1.N1CCC[C@H]1C(O)=O.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I>[Br:1][C:2]1[S:3][C:4]([N:10]2[CH:11]=[CH:12][N:13]=[C:9]2[CH3:8])=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 127492-MethylimidazoleHCID 184532,5-DibromothiopheneHCID 145742L-Proline

Product 1

HCID 672605321-(5-bromothiophen-2-yl)-2-methyl-1H-imidazoleYield 31.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

To the solution of 2,5-dibromothiophene (20 g, 82.6 mmol) and 2-methyl-1H-imidazole (4.1 g, 50 mmol) in DMSO (100 mL) was added CuI (3.14 g, 16.5 mmol), L-proline (0.95 g, 8.3 mmol), K2CO3 (22.9 g, 0.165 mol), the resultant mixture was heated to 100° C. under N2 balloon protection overnight. The reaction mixture was filtrated and the filtrate was poured into water, extracted with EtOAc (300 mL×5). The combined organic layers were washed with brine, dried over Na2SO4, and then filtrated, the filtrate was concentrated under reduced pressure, the residue was purified by column chromatography to give desired 1-(5-bromothiophen-2-yl)-2-methyl-1H-imidazole (3.8 g, yield 31.2%).

Workup

  1. filtrationThe reaction mixture was filtrated
  2. additionthe filtrate was poured into water
  3. extractionextracted with EtOAc (300 mL×5)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltrated
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-b418968ebf0341038d9ed172238ad1b6
Source dataset
uspto-grants-2013_11
Patent number
US08586624B2

Reaction notes

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