Water → 3-bromo-4-chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 79552Notes

Reaction equation

HRID 79552 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9]=2[Cl:11])[NH:4][CH:3]=1.[H-].[Na+].[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CN(C=O)C>[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9]=2[Cl:11])[N:4]([S:26]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:28])=[O:27])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 687633973-bromo-4-chloro-5-phenyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 687614313-bromo-4-chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridineYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Bromo-4-chloro-5-phenyl-1H-pyrrolo[2,3-b]pyridine (1.30 g, 4.23 mmol) was placed in DMF (10 mL) at 0° C. NaH (0.203 g, 5.07 mmol) was then added, and the reaction was stirred for 20 minutes. Benzenesulfonyl chloride (0.595 mL, 4.65 mmol) was then added, and the reaction was stirred for 30 minutes at 0° C. The reaction was then poured into water and extracted with EtOAc. The combined organic fractions were dried, filtered, concentrated and purified (2:1 D CM: hexanes) to give 3-bromo-4-chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyri dine (1.80 g, 95.1% yield).

Workup

  1. stirringthe reaction was stirred for 30 minutes at 0° C
  2. extractionextracted with EtOAc
  3. customThe combined organic fractions were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified (2:1 D CM: hexanes)

Sources & evidence

ORD record
ord-e99f3cc9b5bf46b08290d7f99b68c566
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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