2-Thiophenesulfonyl chloride → Ethyl 4-methyl-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylate

HRID 1851474Notes

Reaction equation

HRID 1851474 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:16])=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2.[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[S:22](Cl)(=[O:24])=[O:23]>N1C=CC=CC=1>[CH3:16][C:5]1[CH:4]=[CH:3][C:2]([NH:1][S:22]([C:18]2[S:17][CH:21]=[CH:20][CH:19]=2)(=[O:24])=[O:23])=[C:10]2[C:6]=1[CH:7]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:9]2

Participants

4

Reactant 2

HCID 855182-Thiophenesulfonyl chlorideHCID 57476149ethyl 7-amino-4-methyl-1H-indole-2-carboxylate

Product 1

HCID 57476010Ethyl 4-methyl-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylateYield 81%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixed solution of ethyl 7-amino-4-methyl-1H-indole-2-carboxylate (0.71 g) and pyridine (20 mL) was added 2-thiophenesulfonyl chloride (0.78 g) under ice-cooling, and the mixture was stirred at room temperature for 2 days. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate, washed with aqueous citric acid solution, aqueous sodium hydrogencarbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=5:95-20:80), and the obtained crystals were recrystallized from ethyl acetate-hexane to give the title compound (957 mg, yield 81%) as colorless needle crystals. melting point 180-181° C.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed with aqueous citric acid solution, aqueous sodium hydrogencarbonate solution and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe obtained crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-7a7924eb4fbf4590801f5e7c864b9dd3
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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