HCID 16128050, compound → HCID 67180116, compound

HRID 2362234Notes

Reaction equation

HRID 2362234 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH2:10][C:11](=O)[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4][CH:3]=1.[N:21]1([C:26]2[CH:27]=[CH:28][C:29]([NH2:32])=[N:30][CH:31]=2)[CH:25]=[CH:24][N:23]=[CH:22]1>C(O)C.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Zn+2]>[N:21]1([C:26]2[CH:27]=[CH:28][C:29]([N:32]3[C:8]([C:5]4[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=4)=[CH:9][CH:10]=[C:11]3[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:30][CH:31]=2)[CH:25]=[CH:24][N:23]=[CH:22]1

Participants

5

Reactant 2

HCID 16128050HCID 16128050, compoundHCID 58297650Ethyl 7-(4-bromophenyl)-4,7-dioxoheptanoate

Product 1

HCID 67180116HCID 67180116, compoundYield 7.2%

Reagents, catalysts & solvents 2

HCID 104671Zinc trifluoromethanesulfonateCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl 7-(4-bromophenyl)-4,7-dioxoheptanoate (5B) (2.56 g, 7.5 mmol) and 5-(1H-imidazol-1-yl)pyridin-2-amine (1.20 g, 7.5 mmol) in 15 mL of ethanol was added Zn(OTf)2 (8.18 g, 22.5 mmol). The resultant mixture was heated at 120° C. for 4 h under microwave irradiation and then concentrated to dryness. The resultant residue was dissolved in EA, washed with water and brine, dried over MgSO4, concentrated and purified by silica gel column chromatography (PE:EA=6:1) to afford ethyl 3-(1-(5-(1H-imidazol-1-yl)pyridin-2-yl)-5-(4-bromophenyl)-1H-pyrrol-2-yl)propanoate as a brown oil (250 mg, 7.1%).

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe resultant residue was dissolved in EA
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (PE:EA=6:1)

Sources & evidence

ORD record
ord-49f28482e28149f1bf457b2ccc3727d5
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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