Sodium Carbonate → methyl 5-(2-chloro-4-fluorophenyl)-4-methyl-1H-pyrrole-3-carboxylate

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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]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1B(O)O.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]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[C:2]1[NH:6][CH:5]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[C:3]=1[CH3:11]

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

A mixture of methyl 5-bromo-4-methyl-1H-pyrrole-3-carboxylate (0.63 g, 2.8 mmol), (2-chloro-4-fluorophenyl)boronic acid (1.0 g, 5.7 mmol), Na2CO3 (0.91 g, 8.6 mmol) and palladium tetrakis(triphenylphosphine) (0.17 g, 0.14 mmol) in toluene/water (10:1, 25 ml) was stirred at 110° C. for 9.0 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 (6:1 to 1:1 hexane:ethyl acetate) to give the title compound (634 mg, 84%) as a white 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 (6:1 to 1:1 hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag: ord-89a792b4cf984429928c46ec9715c495
Quelldatensatz: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08487117B2

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