Potassium Carbonate → [6-Methoxy-2'-(2-oxo-oxazolidin-3-ylmethyl)-4'-trifluoromethyl-biphenyl-3-yl]-acetic acid methyl ester

HRID 456193

Reaktionsgleichung

Reaktionsgleichung von HRID 456193
Br[C:2]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:3]=1[CH2:4][N:5]1[CH2:9][CH2:8][O:7][C:6]1=[O:10].[CH3:19][O:20][C:21](=[O:40])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25](B2OC(C)(C)C(C)(C)O2)[CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.C(Cl)Cl.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:19][O:20][C:21](=[O:40])[CH2:22][C:23]1[CH:24]=[C:25]([C:2]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:3]=2[CH2:4][N:5]2[CH2:9][CH2:8][O:7][C:6]2=[O:10])[C:26]([O:29][CH3:30])=[CH:27][CH:28]=1

Komponenten

8

Edukt 3

HCID 11430Potassium CarbonateHCID 57576289Methyl 2-(4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)acetateHCID 668919133-(2-Bromo-5-trifluoromethyl-benzyl)-oxazolidin-2-one

Produkt 1

HCID 66889230[6-Methoxy-2'-(2-oxo-oxazolidin-3-ylmethyl)-4'-trifluoromethyl-biphenyl-3-yl]-acetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

3-(2-Bromo-5-trifluoromethyl-benzyl)-oxazolidin-2-one (0.234 g, 0.71 mmol), [4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid methyl ester (0.181 g, 0.59 mmol), and potassium carbonate (0.209 g, 1.48 mmol) were combined in DME (2.5 mL) and H2O (1.2 mL) and purged with N2 for 30 minutes. Tetrakis(triphenylphosphine)palladium (0) (0.069 g, 0.06 mmol) was added, and the reaction was stirred at 90° C. for 4 hours. After cooling to room temperature, the mixture was diluted with CH2Cl2 and H2O. The aqueous layer was separated and extracted with CH2Cl2, and the combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (0-50% EtOAc in hexanes) to give the title compound.

Aufarbeitung

  1. customH2O (1.2 mL) and purged with N2 for 30 minutes
  2. temperatureAfter cooling to room temperature
  3. customThe aqueous layer was separated
  4. extractionextracted with CH2Cl2
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (0-50% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-676dbf17698d417ba949f42254c57f96
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497381B2

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