Ethylene Glycol → HCID 118036781, 화합물

HRID 1778038노트

반응식

HRID 1778038 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 118036781HCID 118036781, 화합물

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

반응 조건

온도
80 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-3dcf9456861f402eb3a64308ea589e06
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266883B2

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