Methanesulfonic Acid → Ethyl 4-[(3-chlorophenyl)amino]-1-ethyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylate

HRID 733745Notes

Reaction equation

HRID 733745 reaction equation
Cl[C:2]1[C:7]2[CH:8]=[CH:9][N:10]([CH2:11][CH3:12])[C:6]=2[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][N:3]=1.[Cl:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22].CS(O)(=O)=O>O1CCOCC1>[Cl:18][C:19]1[CH:20]=[C:21]([NH:22][C:2]2[C:7]3[CH:8]=[CH:9][N:10]([CH2:11][CH3:12])[C:6]=3[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][N:3]=2)[CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 79323-ChloroanilineHCID 57840882Ethyl 4-chloro-1-ethyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylate

Product 1

HCID 57840969Ethyl 4-[(3-chlorophenyl)amino]-1-ethyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of ethyl 4-chloro-1-ethyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylate (0.095 g), 3-chloroaniline (0.079 ml) and methanesulfonic acid (0.049 ml) in 1,4-dioxan (2.5 ml) was irradiated at 180° C. for 30 minutes with microwaves. The residue was partitioned between ethyl acetate and water, the aqueous was separated, basified with an aqueous 2M sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated to afford the title compound as a brown oil (0.160 g).

Workup

  1. customwas irradiated at 180° C. for 30 minutes with microwaves
  2. customThe residue was partitioned between ethyl acetate and water
  3. customthe aqueous was separated
  4. extractionextracted three times with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-c22f734f7a3f4c35a0875921709e97a5
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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