2-Thiophenesulfonyl chloride → Ethyl 2-{1-(methoxymethyl)-7-[(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazole-5-carboxylate

HRID 1851376Notes

Reaction equation

HRID 1851376 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][O:12][CH3:13])[C:8]([C:14]1[S:15][C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][N:18]=1)=[CH:7]2.[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[S:29](Cl)(=[O:31])=[O:30]>N1C=CC=CC=1>[CH3:13][O:12][CH2:11][N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[NH:1][S:29]([C:25]2[S:24][CH:28]=[CH:27][CH:26]=2)(=[O:31])=[O:30])[CH:7]=[C:8]1[C:14]1[S:15][C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][N:18]=1

Participants

4

Reactant 2

HCID 855182-Thiophenesulfonyl chlorideHCID 57901657Ethyl 2-[7-amino-1-(methoxymethyl)-1H-indol-2-yl]-1,3-thiazole-5-carboxylate

Product 1

HCID 57901700Ethyl 2-{1-(methoxymethyl)-7-[(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazole-5-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of ethyl 2-[7-amino-1-(methoxymethyl)-1H-indol-2-yl]-1,3-thiazole-5-carboxylate (2.18 g) and pyridine (25 mL) was added thiophene-2-sulfonyl chloride (1.50 g) at 0° C., and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated, 10% aqueous citric acid solution 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 subjected to silica gel column chromatography and the title compound (2.19 g, yield 70%) was obtained as yellow crystals from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio). melting point 133-134° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition10% aqueous citric acid solution was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0ee45517b648483ea7772f4857e647fb
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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