Phosphorus oxychloride → Methyl 4-chloro-1-methyl-1H-pyrrolo(3,2-c)pyridine-7-carboxylate

HRID 733691노트

반응식

HRID 733691 반응식
[CH3:1][N:2]1[C:10]2[C:9]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][NH:7][C:6](=O)[C:5]=2[CH:4]=[CH:3]1.P(Cl)(Cl)([Cl:18])=O>>[Cl:18][C:6]1[C:5]2[CH:4]=[CH:3][N:2]([CH3:1])[C:10]=2[C:9]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][N:7]=1

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 44475352Methyl 4,5-dihydro-1-methyl-4-oxo-1H-pyrrolo[3,2-C]pyridine-7-carboxylate

생성물 1

HCID 44475508Methyl 4-chloro-1-methyl-1H-pyrrolo(3,2-c)pyridine-7-carboxylate

실험 절차

A suspension of methyl 1-methyl-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxylate (47.4 g) in phosphorus oxychloride (64.4 ml) was heated to reflux and stirred for 50 minutes then allowed to cool. The phosphorus oxychloride was removed in vacuo and the residue partitioned between dichloromethane (600 ml) and saturated sodium carbonate (600 ml). The aqueous layer was separated and further extracted with dichloromethane (600 ml). The organic layers were combined, dried (MgSO4) and the solvent removed. The residue was purified by column chromatography on a Biotage silica column (800 g) eluting with dichloromethane to yield the title compound as a white solid (42.7 g).

후처리

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureto cool
  4. customThe phosphorus oxychloride was removed in vacuo
  5. customthe residue partitioned between dichloromethane (600 ml) and saturated sodium carbonate (600 ml)
  6. customThe aqueous layer was separated
  7. extractionfurther extracted with dichloromethane (600 ml)
  8. dry with materialdried (MgSO4)
  9. customthe solvent removed
  10. customThe residue was purified by column chromatography on a Biotage silica column (800 g)
  11. washeluting with dichloromethane

출처 및 근거

ORD 기록
ord-619bfb3e34d04876a89e5055c9347072
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589206B2

반응 노트

불러오는 중…