2-Thiophenecarboxylic acid, 3-(chlorosulfonyl)-, methyl ester → HCID 57901572, compound

HRID 1851470Notes

Reaction equation

HRID 1851470 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][O:17][C:18]([C:20]1[S:21][CH:22]=[CH:23][C:24]=1[S:25](Cl)(=[O:27])=[O:26])=[O:19]>N1C=CC=CC=1>[CH3:16][O:17][C:18]([C:20]1[S:21][CH:22]=[CH:23][C:24]=1[S:25]([NH: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)(=[O:27])=[O:26])=[O:19]

Participants

4

Reactant 2

HCID 27367332-Thiophenecarboxylic acid, 3-(chlorosulfonyl)-, methyl esterHCID 111381941H-Indole-2-carboxylic acid, 7-amino-, ethyl ester

Product 1

HCID 57901572HCID 57901572, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of ethyl 7-amino-1H-indole-2-carboxylate (0.30 g) and pyridine (5 mL) was added 2-methoxycarbonyl-3-thiophenesulfonyl chloride (0.42 g) at 4° C., and the mixture was stirred at room temperature for 2 days. The reaction mixture was concentrated, diluted with ethyl acetate, washed with aqueous citric acid solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:4-ethyl acetate.), and the obtained crystals were washed with ethyl acetate-hexane to give the title compound (550 mg, yield 92%) as pale-yellow crystals. melting point 173-174° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with aqueous citric acid solution, water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washthe obtained crystals were washed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-1ef78a2907b343fa9cfc1b340889815b
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

Loading…