Benzenesulfonyl chloride → 1-(Benzenesulfonyl)-4-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine

HRID 2089024Notes

Reaction equation

HRID 2089024 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]2[NH:10][CH:11]=[C:12]([I:13])[C:5]=12.[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C.O>[Cl:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]2[N:10]([S:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:22])=[O:21])[CH:11]=[C:12]([I:13])[C:5]=12

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 115508744-Chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 583959161-(Benzenesulfonyl)-4-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridineYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 95% sodium hydride (28 mg, 1.1 mmol) and 4-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine (278 mg, 1.0 mmol) in 10 mL DMF was added benzenesulfonyl chloride (194 mg, 1.1 mmol) and the reaction mixture stirred for 2.5 hours then diluted with water and the resulting precipitate collected by filtration to give the title compound in 83% yield. MS (ESI+) m/z 418.9 (M+H)+

Workup

  1. filtrationthe resulting precipitate collected by filtration

Sources & evidence

ORD record
ord-5081d8fb6cfc489c837560f2179586d9
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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