4-Toluenesulfonyl chloride → 4-Bromo-1-(4-methylbenzene-1-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 871099Notes

Reaction equation

HRID 871099 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.[OH-].[Na+]>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:17]([C:14]3[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=3)(=[O:19])=[O:18])[CH:9]=[CH:10][C:3]=12

Participants

8

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 222736434-Bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 378186494-Bromo-1-(4-methylbenzene-1-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 4

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 4-bromo-1H-pyrrolo[2,3-b]pyridine (15 g, 76 mmol) and p-toluenesulfonyl chloride (21.77 g, 114 mmol) in toluene (200 mL) was added a solution of tetrabutylammonium hydrogen sulfate (2.58 g, 7.61 mmol) in water (10 mL) and the mixture was cooled to 0° C. A solution of sodium hydroxide (9.13 g, 228 mmol) in water (30 mL) was added and the mixture was stirred at room temperature for 16 hours. The mixture was diluted with ethyl acetate and the solution was washed with saturated sodium chloride solution. The organic layer was dried over sodium sulfate, filtered and concentrated to give the title compound.

Workup

  1. washthe solution was washed with saturated sodium chloride solution
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3c994188171a49e2be2f378032d7b7fa
Source dataset
uspto-grants-2015_03
Patent number
US08969375B2

Reaction notes

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