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

HRID 1675063Notes

Reaction equation

HRID 1675063 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=[CH:2]1.C1N2CN3CN(C2)CN1C3.[C:20](O)(=[O:22])C>O>[NH:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[C:3]([CH:20]=[O:22])=[CH:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4101HexamethylenetetramineHCID 92205-Azaindole

Product 1

HCID 179815751H-Pyrrolo[3,2-c]pyridine-3-carbaldehydeYield 4.65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1H-pyrrolo[3,2-c]pyridine (2.95 g, 25 mmol) and hexamethylenetetramine (5.26 g, 37.50 mmol) in acetic acid (25 mL) and water (50 mL) was heated under reflux for 4 hours. The reaction mixture was evaporated and the residue was purified by MPLC silica chromatography, elution gradient 5 to 10% ammonia-methanol in DCM. Product containing fractions were evaporated to dryness and triturated with MeCN to afford 1H-pyrrolo[3,2-c]pyridine-3-carbaldehyde (0.170 g, 4.65%) as a white crystalline solid.

Workup

  1. temperatureunder reflux for 4 hours
  2. customThe reaction mixture was evaporated
  3. customthe residue was purified by MPLC silica chromatography, elution gradient 5 to 10% ammonia-methanol in DCM
  4. additionProduct containing fractions
  5. customwere evaporated to dryness
  6. customtriturated with MeCN

Sources & evidence

ORD record
ord-ad6d325f82b94b1f8be52d3a646dcae2
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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