Water → 5-Bromo-3-chloro-4-methyl-1H-pyrrolo[2,3-b]pyridine

HRID 2088972Notes

Reaction equation

HRID 2088972 reaction equation
[Br:1][C:2]1[C:3]([CH3:11])=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[Cl:12]N1C(=O)CCC1=O.O>O1CCCC1>[Br:1][C:2]1[C:3]([CH3:11])=[C:4]2[C:10]([Cl:12])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 401522575-bromo-4-methyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 534129335-Bromo-3-chloro-4-methyl-1H-pyrrolo[2,3-b]pyridineYield 96.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound obtained in Step 3 of Example 36 (323 mg) was dissolved in tetrahydrofuran (6 ml). N-Chlorosuccinimide (225 mg) was added and the mixture was stirred at room temperature for three days. Water was added to the reaction solution, followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated to give the title compound (364 mg).

Workup

  1. extractionfollowed by extraction with chloroform
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-58a52b4aa75a439eba2f2414f9bf642e
Source dataset
uspto-grants-2013_05
Patent number
US08436012B2

Reaction notes

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