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Water → 5-Bromo-4-fluoro-1-(phenylsulfonyl)-7-azaindole

HRID 79594
Notes
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Reaction equation

HRID 79594 reaction equation
[Br:1][C:2]1[C:3]([F:11])=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[C:3]([F:11])=[C:4]2[CH:10]=[CH:9][N:8]([S:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:22])=[O:21])[C:5]2=[N:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 534129385-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 687635785-Bromo-4-fluoro-1-(phenylsulfonyl)-7-azaindoleYield 59.4%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

5-Bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridine (5.3 g, 24.7 mmol) was placed in DMF (53 mL) at 0° C. NaH (1.18 g, 29.6 mmol) was then added and stirred for 20 minutes. Benzenesulfonyl chloride (3.47 mL, 27.1 mmol) was then added next, and the reaction was stirred at 0° C. for 30 minutes. Water was then added, and the resulting solid was filtered and dried. The crude solid was then triturated in 1:1 hexane:EtOAc to give 5-bromo-4-fluoro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (5.2 g, 59.4% yield).

Workup

  1. stirringthe reaction was stirred at 0° C. for 30 minutes
  2. filtrationthe resulting solid was filtered
  3. customdried
  4. customThe crude solid was then triturated in 1:1 hexane

Sources & evidence

ORD record
ord-2f42df19529f44c680f36d867b50d86d
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08841304B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes