N-bromobutanimide → 3-Bromo-5-methoxy-1H-pyrrolo[2,3-b]pyridine

HRID 2089016Notes

Reaction equation

HRID 2089016 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[CH:11]=[CH:10][NH:9][C:6]2=[N:7][CH:8]=1.[Br:12]N1C(=O)CCC1=O>O1CCCC1>[Br:12][C:11]1[C:5]2[C:6](=[N:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[NH:9][CH:10]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 103078715-methoxy-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 378187993-Bromo-5-methoxy-1H-pyrrolo[2,3-b]pyridineYield 55.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-methoxy-1H-pyrrolo[2,3-b]pyridine (0.439 g, 2.96 mmol) in tetrahydrofuran (10 mL) was added N-bromosuccinimide (0.527 g, 2.96 mmol) at 0° C. After 90 minutes at 0° C., the reaction was quenched with 30% Na2S2O3 and extracted with EtOAc (2×). The combined organic layers were washed with water, dried and concentrated. The residue was triturated with EtOAc/diethyl ether (1:1) to give 0.375 g of the title compound.

Workup

  1. customthe reaction was quenched with 30% Na2S2O3
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layers were washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was triturated with EtOAc/diethyl ether (1:1)

Sources & evidence

ORD record
ord-87c1426913244ae2a789d8a37f992e00
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

Loading…