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

HRID 1869209Notes

Reaction equation

HRID 1869209 reaction equation
CO[C:3]1[CH:4]=[C:5]([N+:12]([O-])=O)[C:6]([CH2:9][C:10]#N)=[N:7][CH:8]=1.C[CH2:16][OH:17].CCOC(C)=O>[Pd]>[CH3:16][O:17][C:8]1[N:7]=[C:6]2[CH:9]=[CH:10][NH:12][C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21584252Ethanol ethylacetateHCID 68558809HCID 68558809, compound

Product 1

HCID 53243695-methoxy-1H-pyrrolo[3,2-b]pyridineYield 95%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A suspension of (5-methoxy-3-nitro-pyridin-2-yl)-acetonitrile (Maybridge, 986 mg, 5.1 mmol) and Pd/C (10%, 986 mg) in EtOH/EtOAc (95/5, 50 mL) was shaken for 6 hours under H2 (60 PSI) in Parr apparatus. The reaction mixture was then filtered through a celite pad, and the filter cake was washed with EtOAc (20 mL). The filtrate was concentrated, and the residue was dissolved in EtOAc (50 mL), washed with NaHCO3 (saturated solution, 50 mL), dried over MgSO4, filtered, concentrated, and purified via flash chromatography (hexane/EtOAc), affording 5-Methoxy-1H-pyrrolo[3,2-b]pyridine as a white solid (720 mg, 95% yield).

Workup

  1. filtrationThe reaction mixture was then filtered through a celite pad
  2. washthe filter cake was washed with EtOAc (20 mL)
  3. concentrationThe filtrate was concentrated
  4. dissolutionthe residue was dissolved in EtOAc (50 mL)
  5. washwashed with NaHCO3 (saturated solution, 50 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified via flash chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-0887a6530202476f86585c5be306c08c
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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