Cesium carbonate → 1-(2-(6-(4-oxazol-5-yl-phenoxy)-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

HRID 13267

Reaktionsgleichung

Reaktionsgleichung von HRID 13267
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][CH:11]=[N:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[OH:19][C:20]1[C:21]([CH:43]2[CH2:47][CH2:46][CH2:45][N:44]2[C:48](=[O:50])[CH3:49])=[CH:22][C:23]2[N:27]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[C:26]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=3)=[N:25][C:24]=2[CH:42]=1.[Cl-].[NH4+]>[Cu]=O.N1C=CC=CC=1>[O:12]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([O:19][C:20]3[C:21]([CH:43]4[CH2:47][CH2:46][CH2:45][N:44]4[C:48](=[O:50])[CH3:49])=[CH:22][C:23]4[N:27]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[C:26]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=5)=[N:25][C:24]=4[CH:42]=3)=[CH:3][CH:4]=2)=[CH:9][N:10]=[CH:11]1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 27764185-(4-Bromophenyl)-1,3-oxazoleHCID 231452771-(2-(6-hydroxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

Produkt 1

HCID 231453191-(2-(6-(4-oxazol-5-yl-phenoxy)-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14829Copper oxideKatalysatorHCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

30 mg of 5-(4-bromo-phenyl)-oxazole, 56 mg of cesium carbonate and 15 mg of copper(II) oxide were added to a pyridine (1 ml) solution of 29 mg of 1-(2-(6-hydroxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)pyrrolidin-1-yl)-ethanone, and the reaction liquid was stirred overnight in a sealed tube at 120° C. After cooled, aqueous saturated ammonium chloride solution and saturated saline were added in order to the reaction liquid, and this was extracted with ethyl acetate and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=12/1) to obtain the entitled compound as a yellow oily substance.

Aufarbeitung

  1. customthe reaction liquid
  2. temperatureAfter cooled
  3. extractionthis was extracted with ethyl acetate
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated away under reduced pressure
  6. customthe resulting residue was purified
  7. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=12/1)
  8. customto obtain the entitled compound as a yellow oily substance

Quellen und Nachweise

ORD-Eintrag
ord-492abe89052645c7b2d6ded90f622a3c
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728025B2

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