4-Toluenesulfonyl chloride → HCID 67078537, compound

HRID 1626004Notes

Reaction equation

HRID 1626004 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1.[Br:14][C:15]1[C:16]([I:24])=[C:17]2[CH:23]=[CH:22][NH:21][C:18]2=[N:19][CH:20]=1.[Cl-].[NH4+]>CN(C)C=O>[Br:14][C:15]1[C:16]([I:24])=[C:17]2[CH:23]=[CH:22][N:21]([S:10]([C:7]3[CH:8]=[CH:9][C:4]([CH3:3])=[CH:5][CH:6]=3)(=[O:12])=[O:11])[C:18]2=[N:19][CH:20]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 575376705-Bromo-4-iodo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 67078537HCID 67078537, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

55% Sodium hydride (170 mg) and 4-methylbenzenesulfonyl chloride (740 mg) were added to a solution of 5-bromo-4-iodo-1H-pyrrolo[2,3-b]pyridine obtained by the method described in WO 2008/150914 (1.14 g) in N,N-dimethylformamide (12 ml) in an ice bath, and the mixture was stirred at room temperature for 3 hours. An aqueous ammonium chloride solution was added to the reaction solution, and the precipitated solid was collected by filtration and washed with water. This was dissolved in dichloromethane and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (1.68 g).

Workup

  1. customobtained by the method
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with water
  4. dissolutionThis was dissolved in dichloromethane
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8580ed6c1fe44df3a3104d99177f5543
Source dataset
uspto-grants-2014_07
Patent number
US08785438B2

Reaction notes

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