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

HRID 24039

反応式

HRID 24039 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 27946525-Bromo-1-(triisopropylsilyl)-1H-indole収率 92%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-0561702af9fa4419aaedbad71faaa47d
出典データセット
uspto-grants-2005_02
特許番号
US06855722B2

関連ノート

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