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

HRID 1754682Notes

Reaction equation

HRID 1754682 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-e8766a19b9334d43954c37b76c527b17
Source dataset
uspto-grants-2015_10
Patent number
US09169250B2

Reaction notes

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