Pyridine → HCID 57476240, compound

HRID 1960433Notes

Reaction equation

HRID 1960433 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:16][CH3:17])[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24](Cl)(=[O:26])=[O:25].N1C=CC=C[CH:29]=1>>[CH3:17][O:16][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([N:1]([CH3:29])[S:24]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=3)(=[O:26])=[O:25])[CH:3]=1)[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2

Participants

4

Reactant 3

HCID 1049PyridineHCID 3787675Pyridine-2-sulfonyl ChlorideHCID 15399415Ethyl 7-amino-5-methoxy-1H-indole-2-carboxylate

Product 1

HCID 57476240HCID 57476240, compoundYield 68%

Procedure

To a solution of ethyl 7-amino-5-methoxy-1H-indole-2-carboxylate (2.5 g) in pyridine (20 mL) was added 2-pyridinesulfonyl chloride (2.1 g) under ice-cooling, and the mixture was stirred for 2 hr. The reaction mixture was concentrated, water was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The obtained residue was dissolved in N,N-dimethylformamide (20 mL), methyl iodide (1.5 g) and potassium carbonate (2 g) were added, and the mixture was stirred at room temperature for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid and saturated brine, dried (MgSO4), and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give the title compound (2.7 g, yield 68%) as pale-yellow crystals from a fraction eluted with ethyl acetate-hexane (50:50, volume ratio). MS: 390(MH+).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. additionwater was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with saturated brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. dissolutionThe obtained residue was dissolved in N,N-dimethylformamide (20 mL)
  9. additionmethyl iodide (1.5 g) and potassium carbonate (2 g) were added
  10. stirringthe mixture was stirred at room temperature for 3 hr
  11. additionWater was added to the reaction mixture
  12. extractionthe mixture was extracted with ethyl acetate
  13. washThe organic layer was washed with 1N hydrochloric acid and saturated brine
  14. dry with materialdried (MgSO4)
  15. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fd0333d6c0564c4c8aa6b59cbff5e478
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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