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

HRID 2220440Notes

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 1N 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 1N 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-8785eccea5fc4714a37bffcbe5038283
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417047B2

Reaction notes

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