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

HRID 522198Notes

Reaction equation

HRID 522198 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][N:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.S([O-])([O-])(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:10]=[CH:9][N:8]=[C:7]2[N:6]([S:17]([C:14]3[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=3)(=[O:19])=[O:18])[CH:5]=[CH:4][C:3]=12

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridineHCID 11433187Bis(tetrabutylammonium) sulphate

Product 1

HCID 81672684-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a suspension of 4-chloro-7-azaindole (2.32 g, 15.2 mmol) and p-toluenesulfonyl chloride (3.04 g, 15.96 mmol) in toluene (60 mL) and tetrabutylammonium sulfate (0.175 mL, 0.152 mmol, 50% solution in water) was added a solution of sodium hydroxide (0.913 g, 22.8 mmol) in water (36 mL). The biphasic mixture was stirred vigorously overnight, and was partitioned between ethyl acetate and brine. The aqueous layer was separated and extracted with ethyl acetate. The combined organics were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (Teledyne CombiFlash Rf, 0-20% ethyl acetate in hexane) to provide the title compound. MS (DCI/NH3) m/z 307 (M+H)+.

Workup

  1. customwas partitioned between ethyl acetate and brine
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (Teledyne CombiFlash Rf, 0-20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-5070fa44802b47049eb519cd13833671
Source dataset
uspto-grants-2016_05
Patent number
US09328112B2

Reaction notes

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