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

HRID 1783567Notes

Reaction equation

HRID 1783567 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.[CH3:12][O-:13].[Na+].Cl>CO.[Cu]I>[CH3:12][O:13][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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 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

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 4-bromo-7-chloro-6-azaindole (1 g), CuI (0.65 g) and NaOMe (4 mL, 25% in methanol) in MeOH (16 mL) was heated at 110-120° C. for 16 hours in a sealed tube. After cooling to room temperature, the reaction mixture was neutralized with 1N HCl to pH 7. The aqueous solution was extracted with EtOAc (3×30 mL). Then 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 0.3 g of 4-methoxy-7-chloro-6-azaindole, Precursor 2e. MS m/z: (M+H)+ calcd for C8H8ClN2O: 183.03; found 183.09. HPLC retention time: 1.02 minutes (column B).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe aqueous solution was extracted with EtOAc (3×30 mL)
  3. dry with materialThen the 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-21b9013259e34bfeae68c6ae96ec5f1e
Source dataset
uspto-grants-2009_03
Patent number
US07501420B2

Reaction notes

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