4-Toluenesulfonyl chloride → 5-fluoro-4-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine

HRID 2362623Notes

Reaction equation

HRID 2362623 reaction equation
[H-].[Na+].[F:3][C:4]1[C:5]([I:13])=[C:6]2[CH:12]=[CH:11][NH:10][C:7]2=[N:8][CH:9]=1.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>CN(C)C=O>[F:3][C:4]1[C:5]([I:13])=[C:6]2[CH:12]=[CH:11][N:10]([S:20]([C:17]3[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=3)(=[O:22])=[O:21])[C:7]2=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 242292785-Fluoro-4-iodo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 670034545-fluoro-4-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a stirring suspension of sodium hydride (0.595 g, 24.81 mmol) in N,N-dimethylformamide (74.2 ml) was added a solution of 5-fluoro-4-iodo-1H-pyrrolo[2,3-b]pyridine (5 g, 19.08 mmol, Adesis) in N,N-dimethylformamide (10.60 mL). The mixture was stirred under nitrogen for about 30 minutes. para-Toluenesulfonyl chloride (4.00 g, 20.99 mmol) in N,N-dimethylformamide (10.60 ml) was added, and the reaction stirred at room temperature for about an hour. The reaction was quenched by the slow addition of the reaction mixture to a stirring ice-water solution (about 100 mL). The resulting mixture was filtered, and the solid was collected and dried under vacuum overnight to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 8.28 (s, 1H), 8.09 (d, 1H), 7.98 (d, 2H), 7.43 (d, 2H), 6.67 (d, 1H), 2.35 (s, 3H). MS ESI(+) m/z 416.31 [M+H]+.

Workup

  1. stirringthe reaction stirred at room temperature for about an hour
  2. customThe reaction was quenched by the slow addition of the reaction mixture to a stirring ice-water solution (about 100 mL)
  3. filtrationThe resulting mixture was filtered
  4. customthe solid was collected
  5. customdried under vacuum overnight

Sources & evidence

ORD record
ord-0245737a84664c6388505f29d3f77766
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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