Ethyl 7-(4-methoxyphenyl)-4,7-dioxoheptanoate → HCID 67178681, compound

HRID 2362224Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[C:8]([CH3:13])[CH:7]=1.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=O)[CH2:23][CH2:24][C:25](=O)[CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:18][CH:17]=1>CCO.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Zn+2]>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:12]=[CH:11][C:9]([N:10]2[C:22]([C:19]3[CH:20]=[CH:21][C:16]([O:15][CH3:14])=[CH:17][CH:18]=3)=[CH:23][CH:24]=[C:25]2[CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:8]([CH3:13])[CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 4-(1H-imidazol-2-yl)-2-methylaniline (Method #3) (1.0 g, 5.76 mmol) and ethyl 7-(4-methoxyphenyl)-4,7-dioxoheptanoate (25C) (2.03 g, 6.93 mmol) in EtOH (12 mL) was added Zn(OTf)2 (6.30 g, 17.34 mmol). The mixture was heated by microwave at 120° C. for 5 h. The solvent was removed under reduced pressure and the residue was dissolved in EA, washed with water and brine, dried over MgSO4, filtered, concentrated and purified by silica gel column chromatography (PE:EA=1:1) to afford ethyl 3-(1-(4-(1H-imidazol-2-yl)-2-methylphenyl)-5-(4-methoxyphenyl)-1H-pyrrol-2-yl)propanoate as a brown solid (755 mg, 30%).

Workup

customThe solvent was removed under reduced pressure
dissolutionthe residue was dissolved in EA
washwashed with water and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
custompurified by silica gel column chromatography (PE:EA=1:1)

Sources & evidence

ORD record: ord-b295f42e608e43e0aace4ab6c54d6663
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691816B2

Reaction notes

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