Sodium Carbonate → HCID 58488519, Verbindung

HRID 451358Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 451358
Br[C:2]1[NH:6][CH:5]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[C:3]=1[CH3:11].[F: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]>[F: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

7

Edukt 3

HCID 10340Sodium CarbonateHCID 121094694-Fluoro-2-(trifluoromethyl)benzeneboronic acidHCID 66924763Methyl 5-bromo-4-methyl-1H-pyrrole-3-carboxylate

Produkt 1

HCID 58488519HCID 58488519, VerbindungAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 22272177Toluene waterLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of methyl 5-bromo-4-methyl-1H-pyrrole-3-carboxylate (0.27 g, 1.2 mmol), [4-fluoro-2-(trifluoromethyl)phenyl]boronic acid (0.61 g, 2.9 mmol), Na2CO3 (0.6 g, 5.7 mmol) and palladium tetrakis(triphenylphosphine) (96 mg, 0.083 mmol) in toluene/water (10:1, 10 ml) was stirred at 110° C. for 1.5 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 (3:1 to 1:3 hexane:ethyl acetate) to give the title compound (0.23 mg, 62%) as a pale yellow solid.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe mixture was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated on a rotary evaporator
  5. customThe resulting residue was purified by silica-gel column chromatography (3:1 to 1:3 hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-680b95cf41e847639bb39e5c7d5d48e0
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08487117B2

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