Ethyl Acetate → 5-Bromo-2,3-dimethyl-1H-pyrrolo[2,3-B]pyridine

HRID 500724Notes

Reaction equation

HRID 500724 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH3:11])=[C:9]([CH3:12])[N:8](S(C3C=CC=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.[OH-].[Na+].CCOC(C)=O>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH3:11])=[C:9]([CH3:12])[NH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 684585315-bromo-2,3-dimethyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 193926125-Bromo-2,3-dimethyl-1H-pyrrolo[2,3-B]pyridineYield 72.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5-bromo-2,3-dimethyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (B-6-3) (0.9 g, 2.5 mmol) in THF (30 mL) and MeOH (30 mL) was added aq. NaOH (20%, 19 mL) at room temperature. The mixture was heated to reflux overnight. TLC (Petroleum ether: EtOAc=5:1) showed the reaction was complete. After the solvent was removed under reduced pressure, water (20 mL) and CH2Cl2 (20 mL) were added into the mixture. The organic layer was separated, dried over anhydrous Na2SO4. The mixture was concentrated to give crude mixture which was purified via prep. HPLC to afford 5-bromo-2,3-dimethyl-1H-pyrrolo[2,3-b]pyridine (B-6-4) (0.4 g, 72.4%) as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customAfter the solvent was removed under reduced pressure, water (20 mL) and CH2Cl2 (20 mL)
  4. additionwere added into the mixture
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationThe mixture was concentrated
  8. customto give crude mixture which
  9. customwas purified via prep

Sources & evidence

ORD record
ord-aa17901015e24f51bd91687c8071b466
Source dataset
uspto-grants-2010_08
Patent number
US07772246B2

Reaction notes

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