Anisole → 7-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridine

HRID 1783385Notes

Reaction equation

HRID 1783385 reaction equation
O[C:2]1[N:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.C1(OC)C=CC=CC=1.P(Br)(Br)([Br:23])=O>>[Br:23][C:2]1[N:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2

Participants

4

Reactant 3

HCID 7519AnisoleHCID 24613Phosphorus oxybromideHCID 178493790HCID 178493790, compound

Product 1

HCID 207912447-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridineYield 27.4%

Conditions

Temperature
160 °C

Procedure

To a flask containing 7-hydroxy-4-methoxy-6-azaindole (0.200 g, 1.22 mmol) was added anisole (3 mL) and then POBr3 (1.57 g, 6.09 mmol). The system was purged with Ar and then it was heated at 160° C. (oil bath temperature) for 1 h. The reaction mixture was then allowed to cool to room temperature, quenched with 2M HBr (5 mL) and extracted with methyl t-butyl ether. The aqueous phase was separated and the pH was adjusted to 6-7, after which it was extracted with EtOAc. The resulting organic phase was dried (MgSO4) and evaporated to give a solid residue which was chromatographed (SiO2/5% MeOH-DCM) to afford the title compound (0.076 g, 27%) as a white solid:

Workup

  1. customThe system was purged with Ar
  2. temperatureto cool to room temperature
  3. customquenched with 2M HBr (5 mL)
  4. extractionextracted with methyl t-butyl ether
  5. customThe aqueous phase was separated
  6. extractionafter which it was extracted with EtOAc
  7. dry with materialThe resulting organic phase was dried (MgSO4)
  8. customevaporated
  9. customto give a solid residue which
  10. customwas chromatographed (SiO2/5% MeOH-DCM)

Sources & evidence

ORD record
ord-0c85563ae20744998fe7eb3cad8fa76e
Source dataset
uspto-grants-2009_03
Patent number
US07501419B2

Reaction notes

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