Water → 5-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine

HRID 500728Notes

Reaction equation

HRID 500728 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([CH3:11])[N:8](S(C3C=CC(Br)=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.[OH-].[Na+].O.CCOC(C)=O>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([CH3:11])[NH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 57856305HCID 57856305, compound

Product 1

HCID 454896915-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridineYield 50.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5-bromo-1-(4-bromophenylsulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridine (B-7-5) (4 g, 11.4 mmol) in THF (20 mL) was added aq. NaOH (20 mL) at room temperature. The mixture was heated to reflux overnight. LC-MS showed the reaction was complete. Water (100 mL) and EtOAc (50 mL×3) were added into the mixture. The organic layer was separated, dried over anhydrous Na2SO4 and concentrated to give crude mixture which was purified via prep. HPLC to afford 5-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine (B-7-6) (1.2 g, 50.2%) as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto give crude mixture which
  7. customwas purified via prep

Sources & evidence

ORD record
ord-e670ddefc83048f3830157dbf17b0f59
Source dataset
uspto-grants-2010_08
Patent number
US07772246B2

Reaction notes

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