2-Thiophenesulfonyl chloride → HCID 57476231, compound

HRID 1851478Notes

Reaction equation

HRID 1851478 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH3:16])[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.[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:4]1[CH:5]=[C:6]2[C:10](=[C:2]([NH:1][S:22]([C:18]3[S:17][CH:21]=[CH:20][CH:19]=3)(=[O:24])=[O:23])[CH:3]=1)[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2

Participants

4

Reactant 2

HCID 855182-Thiophenesulfonyl chlorideHCID 21218299HCID 21218299, compound

Product 1

HCID 57476231HCID 57476231, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixed solution of ethyl 7-amino-5-methyl-1H-indole-2-carboxylate (0.60 g) and pyridine (10 mL) was added 2-thiophenesulfonyl chloride (0.66 g) under ice-cooling, and the mixture was stirred at room temperature for 15 hr. 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=3:7-5:5), and the obtained crystals were recrystallized from ethyl acetate-hexane to give the title compound (910 mg, yield 91%) as colorless needle crystals. melting point 168-169° 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-821e049db7bc426d8af712a7bde9ab6e
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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