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

반응식

HRID 13267 반응식
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

참가 물질

7

반응물 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

생성물 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

시약·촉매·용매 2

HCID 14829Copper oxide촉매HCID 1049Pyridine용매

반응 조건

온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-492abe89052645c7b2d6ded90f622a3c
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728025B2

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