Cesium carbonate → tert-butyl {4-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]phenyl}carbamate

HRID 82549

반응식

HRID 82549 반응식
Cl[C:2]1[N:6]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]=1.[OH:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:12][Si:11]([CH3:14])([CH3:13])[CH2:10][CH2:9][O:8][CH2:7][N:6]1[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]=[C:2]1[O:19][C:20]1[CH:21]=[CH:22][C:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[CH:24][CH:25]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 2756771N-Boc-4-hydroxyanilineHCID 597528982-Chloro-1-[[2-(trimethylsilanyl)ethoxy]methyl]-benzimidazole

생성물 1

HCID 58577462tert-butyl {4-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]phenyl}carbamate수율 100.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

A mixture of 2-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazole (8.7 g), tert-butyl 4-hydroxyphenylcarbamate (6.4 g) and cesium carbonate (20 g) in DMF (60 mL) was stirred at 60° C. for 24 h. After cooling to room temperature, to the mixture was added SiO2, the mixture was evaporated, and then the residue was purified by column chromatography (silica gel, eluted with 0%-50% EtOAc in hexane) to give tert-butyl {4-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]phenyl}carbamate (14 g) as brown oil.

후처리

  1. temperatureAfter cooling to room temperature, to the mixture
  2. additionwas added SiO2
  3. customthe mixture was evaporated
  4. customthe residue was purified by column chromatography (silica gel, eluted with 0%-50% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-fc024d9fdbf44f528281c759698cd5ce
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846713B2

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