2-Thiophenesulfonyl chloride → N-[1-(Methoxymethyl)-2-(1,3-thiazol-2-yl)-1H-indol-7-yl]thiophene-2-sulfonamide

HRID 1851371Notes

Reaction equation

HRID 1851371 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH2:13])[CH:6]=[C:5]1[C:14]1[S:15][CH:16]=[CH:17][N:18]=1.[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[S:24](Cl)(=[O:26])=[O:25]>N1C=CC=CC=1>[CH3:1][O:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH:13][S:24]([C:20]2[S:19][CH:23]=[CH:22][CH:21]=2)(=[O:26])=[O:25])[CH:6]=[C:5]1[C:14]1[S:15][CH:16]=[CH:17][N:18]=1

Participants

4

Reactant 2

HCID 855182-Thiophenesulfonyl chlorideHCID 579017321-(Methoxymethyl)-2-(1,3-thiazol-2-yl)-1H-indole-7-amine

Product 1

HCID 57901868N-[1-(Methoxymethyl)-2-(1,3-thiazol-2-yl)-1H-indol-7-yl]thiophene-2-sulfonamideYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 1-(methoxymethyl)-2-(1,3-thiazol-2-yl)-1H-indole-7-amine (1.87 g) and pyridine (10 mL) was added thiophene-2-sulfonyl chloride (1.57 g) at 0° C., and the mixture was stirred at room temperature for 2 hr. 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 (2.69 g, yield 92%) was obtained as yellow crystals from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio). melting point 95-97° 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-6d38aa1525e6470caba0ab1d61542525
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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