Benzenesulfonyl chloride → 1-(Benzenesulfonyl)-4-chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine

HRID 1521995Notes

Reaction equation

HRID 1521995 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[NH:9][CH:10]=[CH:11][C:3]=12.[H-].[Na+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C=O>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[N:9]([S:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:22])=[O:21])[CH:10]=[CH:11][C:3]=12

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 497616114-Chloro-5-fluoro-1H-pyrrolo(2,3-b)pyridine

Product 1

HCID 497616281-(Benzenesulfonyl)-4-chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine (Adesis, 4.60 g, 27.0 mmol) in N,N-dimethylformamide (70 mL) was added 60% sodium hydride in mineral oil (1.186 g, 29.7 mmol) at 0° C. and the mixture was warmed to room temperature and stirred for 30 minutes. Benzenesulfonyl chloride (3.79 mL, 29.7 mmol) was added and after stirring 3 hours, the mixture was quenched with water and aqueous sodium bicarbonate. The suspension was filtered, washed with aqueous sodium bicarbonate, water, and heptanes, and vacuum oven-dried to give the title compound. MS (ESI+) m/z 311.0 (M+H)+.

Workup

  1. stirringafter stirring 3 hours
  2. customthe mixture was quenched with water and aqueous sodium bicarbonate
  3. filtrationThe suspension was filtered
  4. washwashed with aqueous sodium bicarbonate, water, and heptanes, and vacuum
  5. customoven-dried

Sources & evidence

ORD record
ord-c43f5f51c31145aa8b3f47dcb01d327f
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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