Sodium Chloride → HCID 57830157, compound

HRID 500722Notes

Reaction equation

HRID 500722 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH3:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].Br[C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.[Na+].[Cl-]>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH3:11])=[CH:9][N:8]([S:21]([C:18]3[CH:19]=[CH:20][CH:15]=[CH:16][CH:17]=3)(=[O:23])=[O:22])[C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 7396p-Bromobenzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 454802555-Bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 57830157HCID 57830157, compoundYield 40.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine (B-6-1) (1.2 g, 5.68 mmol) in THF (30 mL) was added NaH (0.34 g, 8.5 mmol) under N2 at 0° C., 4-bromophenylsulfonyl chloride (1.2 g, 6.8 mmol) was added 30 minutes later. The mixture was stirred at room temperature for 1.5 h. TLC (Petroleum ether: EtOAc=5:1) showed that the reaction was complete. Saturated aqueous NaCl (10 mL) was added, and the mixture was filtered to give 5-bromo-3-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (B-6-2) (0.8 g) as a white solid. The organic layer was separated from the filtrate, concentrated to 8 mL, then filtered to give 5-bromo-1-(4-bromophenylsulfonyl)-3-methyl-1H-pyrrolo[2,3-b]pyridine (0.5 g). Two batches were combined to give 5-bromo-3-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (B-6-2) (1.3 g, 65.2%) as a white solid.

Workup

  1. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-7ea478b63ec64b2cbdc28253792f28ba
Source dataset
uspto-grants-2010_08
Patent number
US07772246B2

Reaction notes

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