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

HRID 733691Notes

Reaction equation

HRID 733691 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-619bfb3e34d04876a89e5055c9347072
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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