4-Toluenesulfonyl chloride → HCID 66987679, compound

HRID 555727Notes

Reaction equation

HRID 555727 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([I:11])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[S:12](Cl)([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13].[OH-].[Na+]>CCCC[N+](CCCC)(CCCC)CCCC.OS([O-])(=O)=O.C1COCC1.O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([I:11])=[CH:7][N:8]2[S:12]([C:15]2[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 66987354868694-20-6

Product 1

HCID 66987679HCID 66987679, compound

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-chloro-1H-indole (2.0 g, 13.2 mmol) and NIS (4.45 g, 19.8 mmol) in THF (60 mL) is stirred at 0° C. After completion the reaction mixture is quenched by H2O. EtOAc is added and the organic layer is washed with brine, dried over MgSO4 and evaporated in vacuo. Silica gel flash chromatography of the residue affords 6-chloro-3-iodo-1H-indole as a colorless powder. A mixture of 6-chloro-3-iodo-1H-indole (4.14 g, 13.2 mmol), TsCl (3.77 g, 19.8 mmol), TBAHS (672 mg, 1.98 mmol) and NaOH (16.0 g, 400 mmol) in THF (60 mL) and H2O (25 mL) is stirred at RT. After completion the reaction mixture is quenched by H2O. EtOAc is added and the organic layer is washed with brine, dried over MgSO4 and evaporated in vacuo. Re-crystallization from EtOAc of the residue affords the title compound as a colorless powder; ES-MS: M−H=430.0: AtRet=8.66 min.

Workup

  1. customAfter completion the reaction mixture is quenched by H2O
  2. additionEtOAc is added
  3. washthe organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-07e18472923d4335946b1e115e983eb3
Source dataset
uspto-grants-2011_11
Patent number
US08053457B2

Reaction notes

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