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

Reaction equation

HRID 13267 reaction equation
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

Participants

7

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 14829Copper oxideCatalystHCID 1049PyridineSolvent

Conditions

Temperature
120 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-492abe89052645c7b2d6ded90f622a3c
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Linked notes

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