Ammonium Chloride → 7-Chloro-4-methoxy-1H-pyrrolo[2,3-c]pyridine

HRID 899355Notes

Reaction equation

HRID 899355 reaction equation
Br[C:2]1[CH:10]=[N:9][C:8]([Cl:11])=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[NH4+].[Cl-].[CH3:14][O-:15].[Na+]>>[CH3:14][O:15][C:2]1[CH:10]=[N:9][C:8]([Cl:11])=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2

Participants

4

Reactant 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 110317234-Bromo-7-chloro-1H-pyrrolo(2,3-c)pyridine

Product 1

HCID 159870137-Chloro-4-methoxy-1H-pyrrolo[2,3-c]pyridine

Conditions

Temperature
110 °C

Procedure

A mixture of 4-bromo-7-chloro-6-azaindole (6 g), CuBr (3.7 g) and NaOMe (30 mL, 5% in MeOH) was heated at 110° C. for 24 hours in a sealed tube. After cooling to room temperature, the reaction mixture was added to saturated aqueous NH4Cl. The resulting aqueous solution was extracted with EtOAc (3×30 mL). The combined organic layer was dried over MgSO4, filtered and the filtrate was concentrated in vacuo to afford a residue, which was purified by using silica gel chromatography to give 1.8 g of 4-methoxy-7-chloro-6-azaindole, Precursor 2e.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe resulting aqueous solution was extracted with EtOAc (3×30 mL)
  3. dry with materialThe combined organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customto afford a residue, which
  7. customwas purified

Sources & evidence

ORD record
ord-5aa8834dfbaf4d9fb74f556a4b9d16e3
Source dataset
uspto-grants-2008_04
Patent number
US07354924B2

Reaction notes

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