1,8-Diazabicyclo(5.4.0)undec-7-ene → ethyl 1-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrrole-2-carboxylate

HRID 2167400Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8](/[CH:15]=[CH:16]/[C:17](=O)[C:18]([F:21])([F:20])[F:19])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.C1CCN2C(=NCCC2)CC1>CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:15]=[CH:16][C:17]([C:18]([F:21])([F:20])[F:19])=[C:9]2[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of (E)-ethyl 2-((4-chlorophenyl)(4,4,4-trifluoro-3-oxobut-1-en-1-yl)amino)acetate (0.95 g, 2.83 mmol) in EtOAc (20 mL) was added DBU (0.85 mL, 5.66 mmol) and the resulting mixture heated in a sealed tube for 90 min at 120° C. The resulting mixture was cooled to room temperature, diluted with EtOAc (80 mL) and washed with 5% KHSO4 (2×80 mL) and brine (80 mL). The organic layer was concentrated and the residue purified by elution from a 25-g silica cartridge with 0-20% EtOAc/heptane to yield ethyl 1-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrrole-2-carboxylate as a white solid.

Workup

temperatureThe resulting mixture was cooled to room temperature
washwashed with 5% KHSO4 (2×80 mL) and brine (80 mL)
concentrationThe organic layer was concentrated
customthe residue purified by elution from a 25-g silica cartridge with 0-20% EtOAc/heptane

Sources & evidence

ORD record: ord-5113634584d34f21978ed4cb767492d5
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045454B2

Reaction notes

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