Hydrochloric Acid → 5-Bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine

HRID 500720Notes

Reaction equation

HRID 500720 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH3:11])=[C:9]([Si](C)(C)C)[NH:8][C:5]2=[N:6][CH:7]=1.Cl>C1COCC1>[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

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57856278HCID 57856278, compound

Product 1

HCID 454802555-Bromo-3-methyl-1H-pyrrolo[2,3-b]pyridineYield 53.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-3-methyl-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridin (B-5-3) (5 g, 17.8 mmol) in THF (50 mL) was added 2 N HCl (20 mL). The mixture was stirred at reflux overnight. HPLC showed the reaction was complete. After the mixture was concentrated under reduced pressure, the residue was dissolved in aqueous NaHCO3 (20 mL) and extracted with EtOAc (10 mL×3). The organic layer was washed with saturated aqueous NaCl, dried over Na2SO4 and concentrated to give crude product, which was purified via prep. HPLC to give 5-bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine (B-5-4) (2 g, 53.2%) as a pale solid.

Workup

  1. temperatureat reflux overnight
  2. concentrationAfter the mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in aqueous NaHCO3 (20 mL)
  4. extractionextracted with EtOAc (10 mL×3)
  5. washThe organic layer was washed with saturated aqueous NaCl
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customto give crude product, which
  9. customwas purified via prep

Sources & evidence

ORD record
ord-ee0a062bd501410d9f7f44b1db6eb660
Source dataset
uspto-grants-2010_08
Patent number
US07772246B2

Reaction notes

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