Phosphorodichloridic acid, phenyl ester → Methyl 4-chloro-1-methyl-1H-pyrrolo(3,2-c)pyridine-7-carboxylate

HRID 733718Notes

Reaction equation

HRID 733718 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]2[N:14]([CH3:15])[CH:13]=[CH:12][C:7]=2[C:8](=O)[NH:9][CH:10]=1)=[O:4].P(Cl)([Cl:25])(OC1C=CC=CC=1)=O>>[CH3:1][O:2][C:3]([C:5]1[C:6]2[N:14]([CH3:15])[CH:13]=[CH:12][C:7]=2[C:8]([Cl:25])=[N:9][CH:10]=1)=[O:4]

Participants

3

Reactant 2

HCID 13038Phosphorodichloridic acid, phenyl esterHCID 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

1-Methyl-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acid methyl ester (1.25 g) and phenyl dichlorophosphate (12 ml) were heated at 180° C. under argon for 30 minutes. The reaction was allowed to cool at which point a precipitate formed. This was filtered off and washed with diethyl ether to yield the title compound as a grey solid (1.2 g).

Workup

  1. temperatureto cool at which point a precipitate
  2. customformed
  3. filtrationThis was filtered off
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-2de4e85a6cc647b6bbfdfbfdcbbd7bc4
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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