Sulfuric acid magnesium salt (1:1) → 5-Bromo-1-(triisopropylsilyl)-1H-indole

HRID 8336

反応式

HRID 8336 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[H-].[Na+].[CH:13]([Si:16](Cl)([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])([CH3:15])[CH3:14].[O-]S([O-])(=O)=O.[Mg+2]>C(Cl)Cl.CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([Si:16]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:13]([CH3:15])[CH3:14])[CH:6]=[CH:5]2

参加物

8

反応物 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 24758Sodium hydrideHCID 249055-BromoindoleHCID 139400Triisopropylsilyl chloride

生成物 1

HCID 27946525-Bromo-1-(triisopropylsilyl)-1H-indole収率 85%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

5-Bromoindole (3.92 g; 20 mmol) was dissolved in DCM (100 mL) and DMF (1 mL). NaH (0.88 g, 22 mmol; 60% in oil) was added to the cooled solution. After stirring for 15 minutes, triisopropylsilyl chloride (3.86 g, 20 mmol) was added dropwise to the reaction mixture. After 3 h, water (1 mL) was added, followed by MgSO4. The mixture was filtered and concentrated and the residue put through a silica column with hexane as eluent. The product was obtained as a pale yellow oil (5.96 g, 17 mmol; yield 85%). 1H NMR (CDCl3) δ 1.13 (18 H, d, J=8), 1.67 (3 H, m), 6.55 (1 H, d, J=3), 7.21 (1 H, dd, J=9, 2), 7.24 (1 H, d, J=3), 7.36 (1 H, d, J=9) and 7.74 (1 H, d, J=2).

後処理

  1. waitAfter 3 h
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. customThe product was obtained as a pale yellow oil (5.96 g, 17 mmol; yield 85%)

出典と根拠

ORDレコード
ord-8008fa54facc4b4e9dcdeff3d5d00384
出典データセット
uspto-grants-2006_08
特許番号
US07087750B2

関連ノート

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