2-Thiophenesulfonyl chloride → (Z)-N-[3-[2,3-Dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]phenyl]-2-thiophenesulfonamide

HRID 382025Notes

Reaction equation

HRID 382025 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2/[C:10](=[CH:18]/[C:19]2[NH:20][CH:21]=[CH:22][CH:23]=2)/[C:11](=[O:17])[NH:12]3)[CH:5]=[CH:6][CH:7]=1.[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[S:29](Cl)(=[O:31])=[O:30]>N1C=CC=CC=1>[O:17]=[C:11]1[NH:12][C:13]2[C:9](/[C:10]/1=[CH:18]/[C:19]1[NH:20][CH:21]=[CH:22][CH:23]=1)=[C:8]([C:4]1[CH:3]=[C:2]([NH:1][S:29]([C:25]3[S:24][CH:28]=[CH:27][CH:26]=3)(=[O:31])=[O:30])[CH:7]=[CH:6][CH:5]=1)[CH:16]=[CH:15][CH:14]=2

Participants

4

Reactant 2

HCID 855182-Thiophenesulfonyl chlorideHCID 9819193(Z)-4-(3-aminophenyl)-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one

Product 1

HCID 15551262(Z)-N-[3-[2,3-Dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]phenyl]-2-thiophenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A suspension of (Z)-4-(3-aminophenyl)-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (27 mg, 0.090 mmol) (from Example 4 supra) in 1.5 mL of pyridine (Fisher Scientific) was treated dropwise with 2-thiophenesulfonyl chloride (19 mg, 0.104) (Aldrich). The reaction mixture was stirred at room temperature for 30 min and then directly purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 20% ethyl acetate-hexanes then 40% ethyl acetate-hexanes elution) to provide a crude yellow solid. Recrystallization from chloroform-pentane provided pure (Z)-N-[3-[2,3-dihydro-2-oxo-3-(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]phenyl]-2-thiophenesulfonamide (17 mg, 42%) as an orange solid (mp 218-220° C.).

Workup

  1. customdirectly purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 20% ethyl acetate-hexanes
  2. wash40% ethyl acetate-hexanes elution)
  3. customto provide a crude yellow solid
  4. customRecrystallization from chloroform-pentane provided pure (Z)-N-[3-[2,3-dihydro-2-oxo-3-(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]phenyl]-2-thiophenesulfonamide (17 mg, 42%) as an orange solid (mp 218-220° C.)

Sources & evidence

ORD record
ord-4620a0d40666462abcfc30faa91c094b
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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