Pyridine → HCID 59135753, compound

HRID 1960362Notes

Reaction equation

HRID 1960362 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][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.[CH3:16][N:17]1[CH:21]=[CH:20][N:19]=[C:18]1[S:22](Cl)(=[O:24])=[O:23].N1C=CC=C[CH:27]=1>>[CH3:27][N:1]([S:22]([C:18]1[N:17]([CH3:16])[CH:21]=[CH:20][N:19]=1)(=[O:24])=[O:23])[C:2]1[CH:3]=[CH:4][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

Participants

4

Reactant 3

HCID 1049PyridineHCID 111381941H-Indole-2-carboxylic acid, 7-amino-, ethyl esterHCID 116583831-Methyl-1H-imidazole-2-sulfonyl chloride

Product 1

HCID 59135753HCID 59135753, compoundYield 59%

Procedure

To a solution of ethyl 7-amino-1H-indole-2-carboxylate (3 g) in pyridine (30 mL) was added 1-methyl-1H-imidazole-2-sulfonyl chloride (3.6 g) under ice-cooling, and the mixture was stirred for 1 hr. The reaction mixture was concentrated, and the residue was dissolved in ethyl acetate. The solution was washed with water. The ethyl acetate layer was washed with 1N hydrochloric acid, saturated brine and saturated aqueous sodium hydrogencarbonate solution, dried (MgSO4), and concentrated. The obtained residue was dissolved in DMF (30 mL), potassium carbonate (2.1 g) and methyl iodide (2.1 g) were added at room temperature, and the mixture was stirred for 3 hr at room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with 1N hydrochloric acid, saturated brine and saturated aqueous sodium hydrogencarbonate solution, dried (MgSO4), and concentrated. The obtained residue was subjected to silica gel column chromatography to give the title compound (3.0 g, yield 59%) as white crystals from a fraction eluted with ethyl acetate:hexane=50:50. melting point 120° C.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed with water
  5. washThe ethyl acetate layer was washed with 1N hydrochloric acid, saturated brine and saturated aqueous sodium hydrogencarbonate solution
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. dissolutionThe obtained residue was dissolved in DMF (30 mL)
  9. additionpotassium carbonate (2.1 g) and methyl iodide (2.1 g) were added at room temperature
  10. stirringthe mixture was stirred for 3 hr at room temperature
  11. additionWater was added to the reaction mixture
  12. extractionthe mixture was extracted with ethyl acetate
  13. washThe ethyl acetate layer was washed with 1N hydrochloric acid, saturated brine and saturated aqueous sodium hydrogencarbonate solution
  14. dry with materialdried (MgSO4)
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-5b03ab7e584c4a8aaa17802f9aaa499e
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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