Imidazole → 5-(tert-Butyldimethylsilyloxy)-1H-indole

HRID 431172

반응식

HRID 431172 반응식
C(OC(N1C2[C:11](=[CH:12][C:13]([C:17](C)([CH3:24])[O:18][SiH2]C(C)(C)C)=CC=2)C=C1)=O)(C)(C)C.[Si:26](Cl)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27].N1[CH:38]=[CH:37][N:36]=[CH:35]1>CN(C)C=O>[C:29]([Si:26]([CH3:28])([CH3:27])[O:18][C:17]1[CH:13]=[C:12]2[C:37](=[CH:38][CH:24]=1)[NH:36][CH:35]=[CH:11]2)([CH3:32])([CH3:31])[CH3:30]

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 131722897HCID 131722897, 화합물

생성물 1

HCID 222508175-(tert-Butyldimethylsilyloxy)-1H-indole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 5-hydroxyindole (1-3, 5.50 g, 41.3 mmol, 1 equiv), tert-butyldimethylsilyl chloride (7.47 g, 49.6 mmol, 1.20 equiv), and imidazole (7.03 g, 103 mmol, 2.50 equiv) in N, N-dimethylformamide (20 mL) was stirred at 23° C. for 20 hours. The reaction mixture was concentrated, and the residue was partitioned between ethyl acetate and water. The organic layer was washed with water (3×), then dried over magnesium sulfate and concentrated. The residue was purified by flash column chromatography (40% dichloromethane in hexanes, then 60% dichloromethane in hexanes) to give 5-(tert-butyl-dimethyl-silanyloxy)-1H-indole as a colorless oil which solidified upon standing. 1H NMR (400 MHz, CDCl3) δ 8.00 (br s, 1H), 7.22 (d, 1H, J=8.7 Hz), 7.17 (t, 1H, J=2.8 Hz), 7.06 (d, 1H, J=2.3 Hz), 6.76 (dd, 1H, J=8.6, 2.3 Hz), 6.44 (m, 1H), 1.00 (s, 9H), 0.19 (s, 6H).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water (3×)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (40% dichloromethane in hexanes

출처 및 근거

ORD 기록
ord-927c00ba7246478192187b25852afda6
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06656942B2

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