Acetic Acid → 1H-Pyrrolo[3,2-b]pyridine-3-carbaldehyde

HRID 1869194Notes

Reaction equation

HRID 1869194 reaction equation
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C1N2CN3CN(C2)CN1C3.[C:20](O)(=[O:22])C>O>[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:20]=[O:22])=[CH:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4101HexamethylenetetramineHCID 92264-Azaindole

Product 1

HCID 179641321H-Pyrrolo[3,2-b]pyridine-3-carbaldehydeYield 56%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1H-pyrrolo[3,2-b]pyridine (947 mg, 8.02 mmol), hexamethylenetetramine (1.7 g, 12 mmol) and acetic acid (7.5 mL) in water (14 mL) was refluxed under N2 for 4 hours. The reaction mixture was cooled to RT, concentrated, and the residue was purified via flash chromatography (DCM/MeOH/NH4OH) affording 1H-Pyrrolo[3,2-b]pyridin-3-carbaldehyde as a white solid (660 mg, 56% yield).

Workup

  1. temperaturewas refluxed under N2 for 4 hours
  2. concentrationconcentrated
  3. customthe residue was purified via flash chromatography (DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-679f0b950c964bb3b554ff7ad92f5f3d
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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