Potassium Carbonate → 1-(3-bromophenyl)-2-[1-(2,2,2-trifluoroethyl)-1H-pyrrol-3-yl]ethane-1,2-dione

HRID 646218Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:16])[C:9]([C:11]2[CH:15]=[CH:14][NH:13][CH:12]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.CC1C=CC(S(O[CH2:28][C:29]([F:32])([F:31])[F:30])(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[N+](CC)(CC)(CC)CC.[Cl-].O.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:16])[C:9]([C:11]2[CH:15]=[CH:14][N:13]([CH2:28][C:29]([F:32])([F:31])[F:30])[CH:12]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-(3-bromophenyl)-2-(1H-pyrrol-3-yl)ethane-1,2-dione (93 mg, 0.33 mmol) in DMF (5.0 mL) was added 2,2,2-trifluoroethyl 4-methylbenzenesulfonate (170 mg, 0.66 mmol), K2CO3 (100 mg, 0.73 mmol) and Et4NCl (5.5 mg, 0.033 mmol) at room temperature. After heating at 80° C. for 3 days, the reaction mixture is cooled, diluted with H2O, EtOAc. The two layers are separated and the aqueous layer is extracted with EtOAc. The combined organic extracts are washed with 1 N HCl aqueous H2O, brine, dried (MgSO4) and concentrated. The crude material is purified by chromatography (silica gel, EtOAc/hexane:20/80) to give the title compound (190 mg, 65%) as a solid. mp: 105-106° C. MS (+) ES: 418 (M+CH3COO)−.

Workup

temperaturethe reaction mixture is cooled
customThe two layers are separated
extractionthe aqueous layer is extracted with EtOAc
washThe combined organic extracts are washed with 1 N HCl aqueous H2O, brine
dry with materialdried (MgSO4)
concentrationconcentrated
customThe crude material is purified by chromatography (silica gel, EtOAc/hexane:20/80)

Sources & evidence

ORD record: ord-5a656aec50794ea6aa61595e8cbcddd9
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705030B2

Reaction notes

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