5-bromo-1H-pyrrolo[2,3-b]pyridine → 5-methoxy-1H-pyrrolo[2,3-b]pyridine

HRID 1367317Notes

Reaction equation

HRID 1367317 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH3:11][O-:12].[Na+]>CN(C)C=O.CO.[Cu]Br>[CH3:11][O:12][C:2]1[CH:3]=[C:4]2[CH:5]=[CH:6][NH:7][C:8]2=[N:9][CH:10]=1

Participants

6

Reactant 2

HCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineHCID 10942334Sodium Methoxide

Product 1

HCID 103078715-methoxy-1H-pyrrolo[2,3-b]pyridineYield 54%

Reagents, catalysts & solvents 3

HCID 24593copper(I) bromideCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 5-bromo-7-azaindole (1 g, 0.005 mol) in N,N-Dimethylformamide (20 mL) and methanol (20 mL) were added sodium methoxide (13 g, 0.24 mol) and Copper (I) bromide (0.7 g, 0.0048 mol) at room temperature. The reaction mixture was stirred at 120° C. under nitrogen for 3 hours. The reaction mixture was concentrated and the residue was dissolved in ethyl acetate and water. The organic layer was collected, washed with a solution of ammonium chloride and ammonium hydroxide (4:1), brine, and dried over magnesium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with ethyl acetate in hexane to provide the compound as a white solid (81, 0.4 g, 50%). MS (ESI) [M+H+]+=149.09.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. customThe organic layer was collected
  4. washwashed with a solution of ammonium chloride and ammonium hydroxide (4:1), brine
  5. dry with materialdried over magnesium sulfate
  6. customAfter removal of solvent
  7. customthe residue was purified by silica gel column chromatography
  8. washeluting with ethyl acetate in hexane

Sources & evidence

ORD record
ord-f74179a67739439fac36211ca4662459
Source dataset
uspto-grants-2011_02
Patent number
US07893075B2

Reaction notes

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