Imidazole → HCID 67180520, compound

HRID 2362235Notes

Reaction equation

HRID 2362235 reaction equation
[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([N:12]3[C:16]([C:17]4[CH:22]=[CH:21][C:20](Br)=[CH:19][CH:18]=4)=[CH:15][CH:14]=[C:13]3[CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:10][CH:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[NH:31]1[CH:35]=[CH:34][N:33]=[CH:32]1.N1CCC[C@H]1C(O)=O.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I.O>[N:31]1([C:20]2[CH:21]=[CH:22][C:17]([C:16]3[N:12]([C:9]4[CH:8]=[CH:7][C:6]([N:1]5[CH:5]=[CH:4][N:3]=[CH:2]5)=[CH:11][N:10]=4)[C:13]([CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:14][CH:15]=3)=[CH:18][CH:19]=2)[CH:35]=[CH:34][N:33]=[CH:32]1

Participants

8

Reactant 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 67180116HCID 67180116, compound

Product 1

HCID 67180520HCID 67180520, compoundYield 21%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a mixture of ethyl 3-(1-(5-(1H-imidazol-1-yl)pyridin-2-yl)-5-(4-bromophenyl)-1H-pyrrol-2-yl)propanoate (29A) (200 mg, 0.43 mmol) and imidazole (35 mg, 0.516 mmol) in DMSO (5 mL) was added L-proline (19.8 mg, 0.172 mmol), CuI (16.4 mg, 0.086 mmol) and K2CO3 (119 mg, 0.86 mmol). The resultant mixture was heated at 150° C. for 5 h under microwave irradiation, poured into water and extracted with EA for 5 times. The combined organic layers were washed with brine, dried over MgSO4, concentrated and purified by silica gel column chromatography (DCM:MeOH=20:1) to afford ethyl 3-(5-(4-(1H-imidazol-1-yl)phenyl)-1-(5-(1H-imidazol-1-yl)pyridin-2-yl)-1H-pyrrol-2-yl)propanoate as a brown oil (40 mg, 21%).

Workup

  1. extractionextracted with EA for 5 times
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography (DCM:MeOH=20:1)

Sources & evidence

ORD record
ord-1c582e5b70cc4ad5b063f1ba42930b7c
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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