Potassium Carbonate → 7-Bromo-1-[(S)-2-(tert-butyldimethyl-silanyloxy)-propyl]-6-oxiranylmethoxy-1H-indazole

HRID 1815962

반응식

HRID 1815962 반응식
[Br:1][C:2]1[C:3]([OH:22])=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][C@@H:12]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH3:13])[N:8]=[CH:7]2.C(=O)([O-])[O-].[K+].[K+].[CH2:29]([CH:31]1[O:33][CH2:32]1)Br>CC(C)=O>[Br:1][C:2]1[C:3]([O:22][CH2:29][CH:31]2[CH2:32][O:33]2)=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][C@@H:12]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:16])[CH3:17])[CH3:13])[N:8]=[CH:7]2

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 1364116817-Bromo-1-[(S)-2-(tert-butyldimethyl-silanyloxy)-propyl]-1H-indazol-6-ol

생성물 1

HCID 867596497-Bromo-1-[(S)-2-(tert-butyldimethyl-silanyloxy)-propyl]-6-oxiranylmethoxy-1H-indazole수율 471.5%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A suspension of the product from Step C (3.66 g, 9.51 mmol), potassium carbonate (1.92 g, 1.46 mmol), and epibromohydrine (1.32 mL, 1.60 mmol) in acetone (200 mL) was heated at reflux for 30 h. The solid was removed by filtration and the filtrate was concentrated to an oil that was purified by chromatography (silica, 2% to 10% EtOAc/hexane) to afford an oil (3.33 g, 79%): LC/MS (+APCI) m/z 441, 443 (M+H).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 30 h
  3. customThe solid was removed by filtration
  4. concentrationthe filtrate was concentrated to an oil that
  5. customwas purified by chromatography (silica, 2% to 10% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-ea57fbdc0e21441aa0466e4cc13e11a3
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06881749B2

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