Sodium Carbonate → methyl 5-[4-chloro-2-(trifluoromethyl)phenyl]-4-methyl-1H-pyrrole-3-carboxylate

HRID 451362Notizen

Reaktionsgleichung

Br[C:2]1[NH:6][CH:5]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[C:3]=1[CH3:11].[Cl:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[C:15]([C:22]([F:25])([F:24])[F:23])[CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O.C(OCC)(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[NH:6][CH:5]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[C:3]=2[CH3:11])=[C:15]([C:22]([F:23])([F:24])[F:25])[CH:14]=1

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

A mixture of methyl 5-bromo-4-methyl-1H-pyrrole-3-carboxylate (0.44 g, 2.0 mmol), [4-chloro-2-(trifluoromethyl)phenyl]boronic acid (0.90 g, 4.0 mmol), Na2CO3 (0.64 g, 6.0 mmol) and palladium tetrakis(triphenylphosphine) (0.12 g, 0.10 mmol) in toluene/water (9:1, 10 ml) was stirred at 110° C. for 2.0 h under N2. The reaction mixture was cooled to room temperature and diluted with ethyl acetate. The mixture was washed with water and brine, then dried over sodium sulfate and concentrated on a rotary evaporator. The resulting residue was purified by silica-gel column chromatography (dichloromethane) to give the title compound (0.41 g, 65%) as a pale yellow solid.

Aufarbeitung

temperatureThe reaction mixture was cooled to room temperature
washThe mixture was washed with water and brine
dry with materialdried over sodium sulfate
concentrationconcentrated on a rotary evaporator
customThe resulting residue was purified by silica-gel column chromatography (dichloromethane)

Quellen und Nachweise

ORD-Eintrag: ord-72fefe348b6a43c5bc1fcddcf9400c17
Quelldatensatz: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08487117B2

Notizen zur Reaktion

Wird geladen…