4-Toluenesulfonyl chloride → 6-Chloro-1-tosyl-1H-indole

HRID 555729ノート

反応式

HRID 555729 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1.[S:13](Cl)([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14]>C1COCC1>[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[S:13]([C:16]2[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=2)(=[O:15])=[O:14])=[CH:6][CH:5]=1

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 871116-Chloroindole

生成物 1

HCID 112436876-Chloro-1-tosyl-1H-indole

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Intermediate 147.3 is prepared in analogy to a published literature procedure (J. Med. Chem. 2006, 49, 3101-3115). 55% of NaH in mineral oil (881 mg, 20.2 mmol) is added to a solution of 6-Chloroindole (3.0 g, 19.8 mmol) in THF (28 mL) at 0° C. After 1 h, TsCl (3.85 g, 20.2 mmol) is added, and the reaction mixture is stirred at RT. After completion, the reaction mixture is quenched by saturated aqueous NaHCO3 and diluted with Et2O. The organic layer is dried over Na2SO4 and evaporated in vacuo to provide crude solid. The crude product is washed with small amount of Et2O to give the title compound as orange crystal; ES-MS: M+=306.1: AtRet=5.60.

後処理

  1. customAfter completion, the reaction mixture is quenched by saturated aqueous NaHCO3
  2. additiondiluted with Et2O
  3. dry with materialThe organic layer is dried over Na2SO4
  4. customevaporated in vacuo
  5. customto provide crude solid
  6. washThe crude product is washed with small amount of Et2O

出典と根拠

ORDレコード
ord-bb43f603388241d0b3b8b9e0b34135fb
出典データセット
uspto-grants-2011_11
特許番号
US08053457B2

反応ノート

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