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

HRID 555729Notes

Reaction equation

HRID 555729 reaction equation
[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

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 871116-Chloroindole

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bb43f603388241d0b3b8b9e0b34135fb
Source dataset
uspto-grants-2011_11
Patent number
US08053457B2

Reaction notes

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