Ethylene Glycol → HCID 118036781, compound

HRID 1778038Notes

Reaction equation

HRID 1778038 reaction equation
[NH:1]1[C:5]2=[N:6][C:7]([CH:10]=[O:11])=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[CH2:12](O)[CH2:13][OH:14].CCCP(=O)=O>CCOC(C)=O.C([O-])(O)=O.[Na+]>[O:11]1[CH2:12][CH2:13][O:14][CH:10]1[C:7]1[N:6]=[C:5]2[NH:1][CH:2]=[CH:3][C:4]2=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 16167369Propylphosphoric anhydrideHCID 247288931H-Pyrrolo[2,3-b]pyridine-6-carbaldehyde

Product 1

HCID 118036781HCID 118036781, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1H-pyrrolo[2,3-b]pyridine-6-carbaldehyde (840 mg, 5.60 mmol), ethylene glycol (3.13 ml, 56.0 mmol) and propylphosphonic anhydride (50% in EtOAc, 3.34 ml, 5.60 mmol) in EtOAc (15 ml) was stirred at 80° C. After 18 h, the reaction mixture was cooled to room temperature, diluted with sat. aq. NaHCO3 and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over Na2SO4 and evaporated. The crude material was applied to a 120 g RediSep® silica column and purified by normal phase chromatography, eluting with EtOAc. Product-containing fractions were combined and evaporated. The residue was triturated with Et2O to give the title compound as an white solid. (UPLC-MS 6) tR 0.66; ESI-MS 191.1 [M+H]+.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. custompurified by normal phase chromatography
  7. washeluting with EtOAc
  8. customevaporated
  9. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-3dcf9456861f402eb3a64308ea589e06
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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