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Potassium hydride → 5-Bromo-3-(1-Methylpiperidin-4-yl)-1-Triisopropylsilylindole

HRID 367356
ノート
印刷プレビュー

反応式

HRID 367356 の反応式
[H-].[K+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1.FC(F)(F)S(O[Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])(=O)=O>O1CCCC1>[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])[CH:8]=[C:7]2[CH:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 82127Potassium hydrideHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 157453445-bromo-3-(1-methylpiperidin-4-yl)-1H-indole

生成物 1

HCID 120859685-Bromo-3-(1-Methylpiperidin-4-yl)-1-Triisopropylsilylindole収率 173.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a 10° C. slurry of potassium hydride (1.6 g, 14.3 mmol, 35% in mineral oil) in tetrahydrofuran (40 mL) was added neat 5-bromo-3-(1-methyl-4-piperidinyl)indole (2.8 g, 9.5 mmol) portionwise over 30 minutes. The resulting reaction mixture was stirred at 0° C. for 1 hour. Triisopropylsilyl trifluoromethanesulfonate (3.1 mL, 11.4 mmol) was added dropwise over 20 minutes and a slight exotherm was observed. After stirring 2 hours at 0° C., the reaction was quenched with ice chips then diluted with water and methylene chloride. The layers were separated and the aqueous layer was extracted with methylene chloride. The organic extracts were combined, washed with brine, dried over sodium sulfate, and concentrated in vacuo to give 7.4 g of a clear colorless oil. Purification by chromatography (florisil, 50:50 methylene chloride:hexanes, then 100% methylene chloride, then 95:5 methylene chloride:methanol) provided 3.6 g (84.1%) of the title compound. MS(FD) 448, 450 (M+).

後処理

  1. customThe resulting reaction mixture
  2. stirringAfter stirring 2 hours at 0° C.
  3. customthe reaction was quenched with ice chips
  4. additionthen diluted with water and methylene chloride
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with methylene chloride
  7. washwashed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-8f63e74f2dda4ebeb6d4c806308e14bf
出典データセット
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06133290

反応ノート

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