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

反応式

HRID 13267 の反応式
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

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 14829Copper oxide触媒HCID 1049Pyridine溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-492abe89052645c7b2d6ded90f622a3c
出典データセット
uspto-grants-2010_06
特許番号
US07728025B2

関連ノート

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