Acetic Acid → 6-phenyl-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde

HRID 1749815Notes

Reaction equation

HRID 1749815 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]3[NH:13][CH:14]=[CH:15][C:10]3=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16](O)(=[O:18])C.C1N2CN3CN(C2)CN1C3.C(=O)([O-])O.[Na+]>O>[C:1]1([C:7]2[N:12]=[C:11]3[NH:13][CH:14]=[C:15]([CH:16]=[O:18])[C:10]3=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 4101HexamethylenetetramineHCID 516892Sodium BicarbonateHCID 866819996-phenyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 866820006-phenyl-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehydeYield 11%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

6-Phenyl-1H-pyrrolo[2,3-b]pyridine (0.10 g, 0.52 mmol) was successively added with acetic acid (0.2 mL), water (0.4 mL), and hexamethylenetetramine (0.11 g, 0.77 mmol), and then the mixture was stirred overnight at 120° C. in a sealed tube. The reaction mixture was cooled to room temperature, and then added with saturated aqueous sodium hydrogencarbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (99:1→99:5)) to obtain a solid containing the objective substance. The solid was washed with a mixed solvent of chloroform and methanol to obtain 6-phenyl-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde (0.013 g, 11%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washthe residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (99:1→99:5))
  7. customto obtain a solid
  8. additioncontaining the objective substance
  9. washThe solid was washed with a mixed solvent of chloroform and methanol

Sources & evidence

ORD record
ord-da0f7810a96d404db5f28814f6ed8609
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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