2-Bromopyridine → {3-[2-((4S,5R)-4-Methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-4-pyridin-2-yl-phenoxy]-phenyl}-acetic acid ethyl ester

HRID 885282Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 885282
[CH2:1]([O:3][C:4](=[O:42])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16](B3OC(C)(C)C(C)(C)O3)=[CH:15][C:14]=2[CH2:28][N:29]2[C@@H:33]([CH3:34])[C@@H:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[O:31][C:30]2=[O:41])[CH:7]=1)[CH3:2].Br[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=1.C(=O)([O-])[O-].[K+].[K+]>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.COCCOC>[CH2:1]([O:3][C:4](=[O:42])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=3)=[CH:15][C:14]=2[CH2:28][N:29]2[C@@H:33]([CH3:34])[C@@H:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[O:31][C:30]2=[O:41])[CH:7]=1)[CH3:2]

Komponenten

6

Edukt 3

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 58237457{3-[2-((4S,5R)-4-Methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-phenyl}-acetic acid ethyl ester

Produkt 1

HCID 58237583{3-[2-((4S,5R)-4-Methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-4-pyridin-2-yl-phenoxy]-phenyl}-acetic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

{3-[2-((4S,5R)-4-Methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-phenyl}-acetic acid ethyl ester (0.1 g, 0.18 mmol), 2-bromopyridine (0.042 g, 0.26 mmol), potassium carbonate (0.061 g, 0.44 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.020 g, 0.02 mmol) were combined in 2:1 DME:H2O (4 mL) and degassed with N2 for 10 minutes. The reaction was then heated to 90° C. for 3.5 hours. The mixture was neutralized to pH 6 with 10% aqueous HCl and extracted with EtOAc. The crude material was purified by silica gel chromatography to give the desired product.

Aufarbeitung

  1. customH2O (4 mL) and degassed with N2 for 10 minutes
  2. extractionextracted with EtOAc
  3. customThe crude material was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-088dcee9803b4c8982d3112f5c47e067
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242145B2

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