Water → 5-Bromo-1-(triisopropylsilyl)-1H-indole

HRID 24039

반응식

HRID 24039 반응식
C[Si](C)(C)N[Si](C)(C)C.[Li].[Br:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[CH:15]2.[CH:21]([Si:24](Cl)([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26])([CH3:23])[CH3:22].O>O1CCCC1>[Br:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([Si:24]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:21]([CH3:23])[CH3:22])[CH:16]=[CH:15]2

참가 물질

6

반응물 4

HCID 962WaterHCID 249055-BromoindoleHCID 139400Triisopropylsilyl chlorideHCID 57426343Lithium bis(trimethylsilyl)amide

생성물 1

HCID 27946525-Bromo-1-(triisopropylsilyl)-1H-indole수율 92%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Lithium hexamethyldisilazane [1.0 M] (44.7 mL, 44.4 mmol) was added to a solution of 5-bromo-1H-indole (7.30 g, 37.0 mmol) in tetrahydrofuran (50 mL) at room temperature. After stirring for 5 minutes, triisopropylsilyl chloride (8.62 g, 44.4 mmol) was added to reaction mixture and stirred for 30 minutes. Water was added to quench the reaction and the solvent was removed under reduced pressure to give the crude mixture, which was purified via column chromatography on silica gel (9:1 Hexane/ethyl acetate) to give the title compound in 92% yield. 1H NMR (CDCl3) δ 7.74 (d, J=1.8, 1H), 7.36 (d, J=8.8 Hz, 1H), 7.22 (m, 2H), 6.55 (d, J=3.1 Hz, 1H), 1.65 (m, 3H), 1.12 (d, J=7.5 Hz, 18H).

후처리

  1. stirringstirred for 30 minutes
  2. customto quench
  3. customthe reaction
  4. customthe solvent was removed under reduced pressure
  5. customto give the crude mixture, which
  6. customwas purified via column chromatography on silica gel (9:1 Hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-0561702af9fa4419aaedbad71faaa47d
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855722B2

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