Methanesulfonic Acid → 4-[(3-Chloro-phenyl)-methyl-amino]-1-methyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acid methyl ester

HRID 733721Notes

Reaction equation

HRID 733721 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](Cl)=[N:9][CH:10]=1)=[O:4].[Cl:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[NH:20][CH3:21].CS(O)(=O)=O>O1CCOCC1>[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]([N:20]([C:19]2[CH:22]=[CH:23][CH:24]=[C:17]([Cl:16])[CH:18]=2)[CH3:21])=[N:9][CH:10]=1)=[O:4]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 1389003-chloro-N-methylanilineHCID 44475508Methyl 4-chloro-1-methyl-1H-pyrrolo(3,2-c)pyridine-7-carboxylate

Product 1

HCID 578407984-[(3-Chloro-phenyl)-methyl-amino]-1-methyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acid methyl esterYield 47.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-chloro-1-methyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acid methyl ester (0.5 g) in 1,4-dioxane (5 ml) was added 3-chloro-N-methyl aniline (0.629 g) and methanesulfonic acid (0.289 ml). The mixture was irradiated under microwave conditions at 180° C. for 30 min. 1,4-dioxane was removed in vacuo and the residue purified by MDAP to give the title compound (350 mg).

Workup

  1. customThe mixture was irradiated under microwave conditions at 180° C. for 30 min
  2. custom1,4-dioxane was removed in vacuo
  3. customthe residue purified by MDAP

Sources & evidence

ORD record
ord-34764c204a7a45dd94fd0bcfd7e9367b
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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