Imidazole → HCID 67175664, compound

HRID 238402Notes

Reaction equation

HRID 238402 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][N:10]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])[C:9]=2[C:18]2[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][C:19]=2[CH3:26])=[CH:4][CH:3]=1.[NH:27]1[CH:31]=[CH:30][N:29]=[CH:28]1.N1CCC[C@H]1C(O)=O.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I>[N:27]1([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:12]=[CH:11][N:10]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])[C:9]=3[C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][C:19]=3[CH3:26])=[CH:4][CH:3]=2)[CH:31]=[CH:30][N:29]=[CH:28]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 67175904HCID 67175904, compound

Product 1

HCID 67175664HCID 67175664, compoundYield 48.9%

Reagents, catalysts & solvents 2

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

Procedure

To a mixture of 3-(3-(4-bromophenyl)-2-(4-cyano-2-methylphenyl)-1H-pyrrol-1-yl)propanoic acid (400 mg, 0.98 mmol) and imidazole (200 mg, 2.94 mol) in DMSO (5 mL) was added L-proline (33.8 mg, 0.294 mmol), CuI (111.7 mg, 0.588 mmol) and K2CO3 (270 mg, 1.96 mmol), then the resultant mixture was stirred at 100° C. overnight. After being cooled down to room temperature, the reaction mixture was filtered, and the filter cake was washed with ethyl acetate (10 mL×3). The combined filtrate was washed with saturated NaHCO3 aqueous solution (30 mL), and the aqueous layer was extracted with ethyl acetate (15 mL×3). The combined organic layers were washed with brine, dried over MgSO4, concentrated. The residue was purified by silica gel column (DCM: MeOH=30:1-20:1) to afford 3-(3-(4-(1H-imidazol-1-yl)phenyl)-2-(4-cyano-2-methylphenyl)-1H-pyrrol-1-yl)propanoic acid (190 mg, yield 48.9%) as a solid.

Workup

  1. filtrationthe reaction mixture was filtered
  2. washthe filter cake was washed with ethyl acetate (10 mL×3)
  3. washThe combined filtrate was washed with saturated NaHCO3 aqueous solution (30 mL)
  4. extractionthe aqueous layer was extracted with ethyl acetate (15 mL×3)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column (DCM: MeOH=30:1-20:1)

Sources & evidence

ORD record
ord-1cd8576f3f944da4a448abaeb46d683f
Source dataset
uspto-grants-2014_02
Patent number
US08642628B2

Reaction notes

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