4-Toluenesulfonyl chloride → 6-Chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine

HRID 1749808Notes

Reaction equation

HRID 1749808 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1.[OH-].[Na+].[S:13](Cl)([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14]>C(Cl)Cl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([S:13]([C:16]3[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 113441186-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 862804116-Chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridineYield 93%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

The synthesis was performed with reference to the known literature (Heterocycles, Vol. 30, p. 627, 1990). A solution of 6-chloro-1H-pyrrolo[2,3-b]pyridine (0.21 g, 1.4 mmol) obtained in Example A46, Step 2 in methylene chloride (10 mL) was successively added with sodium hydroxide (0.17 g, 4.2 mmol), and tetrabutylammonium hydrogensulfate (0.14 g, 0.42 mmol), and the mixture was stirred at room temperature. Then, the reaction mixture was added dropwise with a solution of tosyl chloride (0.32 g, 1.7 mmol) in methylene chloride (5 mL), and then the mixture was stirred overnight. The reaction mixture was extracted with ethyl acetate, and then the resulting organic layer was successively washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was washed with a mixed solvent of ethyl acetate and hexane to obtain 6-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine (0.39 g, 93%).

Workup

  1. stirringthe mixture was stirred overnight
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washthe resulting organic layer was successively washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washthe residue was washed with a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-635c5e6afcbb4a5d84515dc4f35fa600
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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