Methanesulfonic Acid → HCID 44475509, compound

HRID 733719Notes

Reaction equation

HRID 733719 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:21]=[CH:22][CH:23]=1)[NH2:20].CS(O)(=O)=O>O1CCOCC1.CO>[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]([NH:20][C:19]2[CH:21]=[CH:22][CH:23]=[C:17]([Cl:16])[CH:18]=2)=[N:9][CH:10]=1)=[O:4]

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 79323-ChloroanilineHCID 44475508Methyl 4-chloro-1-methyl-1H-pyrrolo(3,2-c)pyridine-7-carboxylate

Product 1

HCID 44475509HCID 44475509, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

4-Chloro-1-methyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acid methyl ester (1.04 g), 3-chloroaniline (0.97 ml) and methanesulfonic acid (0.60 ml) in 1,4-dioxan (10 ml) were irradiated at 180° C. for 30 minutes with microwaves. The solid mass obtained was dissolved in methanol and the solvent evaporated. The residue was dissolved in ethyl acetate and washed with water followed by saturated brine solution then dried (MgSO4)), filtered and evaporated to yield a brown oil (1.6 g). The brown oil was purified by column chromatography on a Biotage® 40M column eluting in 20% ethyl acetate/iso-hexane, to give the title compound as an off-white solid (0.62 g).

Workup

  1. customThe solid mass obtained
  2. customthe solvent evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialthen dried (MgSO4)),
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-8cdba128dd224629bef68f6fd5b6e9a4
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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