Potassium Carbonate → HCID 90411426, compound

HRID 1476700Notes

Reaction equation

HRID 1476700 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:13]1[S:14][CH:15]=[CH:16][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C(OCC)(=O)C.[Cu]I>[C:1]1([C:7]2[N:8]=[CH:9][N:10]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)[CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 138512-BromothiopheneHCID 178418822HCID 178418822, compound

Product 1

HCID 90411426HCID 90411426, compoundYield 3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of 4-phenyl-1H-imidazole (500 mg, 3.47 mmol), 2-bromothiophene (0.4 ml, 4.16 mmol), CuI (131.9 mg, 0.694 mmol, trans-N,N′-dimethylcyclohexanediamine (0.08 ml, 0.694 mmol), and K2CO3 (1.43 g, 10.4 mmol) in dioxane (5 ml) was heated at 110° C. in a sealed tube for 16 hours. The reaction mixture was then diluted with ethyl acetate and filtered. The filtrate was concentrated and purified by column chromatography using 15-20% ethyl acetate/hexanes to yield the desired 4-phenyl-1-(thiophen-2-yl)-1H-imidazole (23 mg, 3%). The HPLC purity of the final product was 99.7%. LC-MS [M+H] 227 (C13H10N2S+H expected 227.06).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-2ac559d6c8d94834a2cfb0431d1c9aff
Source dataset
uspto-grants-2016_08
Patent number
US09402397B2

Reaction notes

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