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

HRID 733738Notes

Reaction equation

HRID 733738 reaction equation
Cl[C:2]1[C:7]2[CH:8]=[CH:9][NH:10][C:6]=2[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][N:3]=1.[Cl:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20].CS(O)(=O)=O>O1CCOCC1>[Cl:16][C:17]1[CH:18]=[C:19]([NH:20][C:2]2[C:7]3[CH:8]=[CH:9][NH:10][C:6]=3[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][N:3]=2)[CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 79323-ChloroanilineHCID 57840913ethyl 4-chloro-1H-pyrrolo[3,2-c]pyridine-7-carboxylate

Product 1

HCID 57840854Ethyl 4-[(3-chlorophenyl)amino]-1H-pyrrolo[3,2-c]pyridine-7-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of ethyl 4-chloro-1H-pyrrolo[3,2-c]pyridine-7-carboxylate (0.49 g), 3-chloroaniline (0.46 ml) and methanesulfonic acid (0.28 ml) in 1,4-dioxan (10 ml) was irradiated at 180° C. for 30 minutes with microwaves. The residue was partitioned between ethyl acetate and water, the aqueous layer 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 solid (0.91 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 layer 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-814bc65728e84ef7adf2e4face7f28b1
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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