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

HRID 1626007Notes

Reaction equation

HRID 1626007 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-18089958fb4b4357bee6616174b7a234
Source dataset
uspto-grants-2014_07
Patent number
US08785438B2

Reaction notes

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