Imidazole → 5-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1H-indazole

HRID 246717

반응식

HRID 246717 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([OH:10])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.N1C=CN=C1.[C:16]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])([CH3:18])[CH3:17]>ClCCl>[Si:20]([O:10][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][N:2]=[CH:3]2)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:22])[CH3:21]

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1014381H-Indazol-5-ol

생성물 1

HCID 580425115-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1H-indazole수율 100%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 1H-indazol-5-ol (5.0 g, 37.3 mol) and imidazole (12.7 g, 186.5 mmol) in dichloromethane (200 mL) was added tert-butylchlorodimethylsilane (16.8 g, 112 mol) and the mixture stirred at room temperature overnight. Then the reaction mixture was washed with brine (3×50 mL) and dried over Na2SO4. The crude mixture was purified by column chromatography (silica gel, 200-300 mesh, EtOAc:petroleum ether=1:10, v/v) to give 5-(tert-Butyldimethylsilyloxy)-1H-indazole (9.5 g, yield 100%) as yellow oil. MS: (M+H)+=249.2; 1H NMR (300 MHz, CDCl3): δ 7.95 (d, 1H, J=1.2 Hz), 7.34 (dt, 1H, J=8.7, 0.75 Hz), 7.12 (s, 1H), 6.97 (dd, 1H, J=8.7, 2.1 Hz), 1.01 (s, 9H), 0.23 (s, 6H).

후처리

  1. washThen the reaction mixture was washed with brine (3×50 mL)
  2. dry with materialdried over Na2SO4
  3. customThe crude mixture was purified by column chromatography (silica gel, 200-300 mesh, EtOAc

출처 및 근거

ORD 기록
ord-e22c54ec47e44d0395cd55b884eec2a9
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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