Triethylamine → (Z)-N-[3-[2,3-dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]phenyl]-4-(phenylsulfonyl)-2-thiophenesulfonamide

HRID 382043Notes

Reaction equation

HRID 382043 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.CCN(CC)CC.[C:31]1([S:37]([C:40]2[CH:41]=[C:42]([S:45](Cl)(=[O:47])=[O:46])[S:43][CH:44]=2)(=[O:39])=[O:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>COCCOC>[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:45]([C:42]3[S:43][CH:44]=[C:40]([S:37]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)(=[O:39])=[O:38])[CH:41]=3)(=[O:46])=[O:47])[CH:7]=[CH:6][CH:5]=1)[CH:16]=[CH:15][CH:14]=2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6255744-(Benzenesulfonyl)thiophene-2-sulfonyl chlorideHCID 9819193(Z)-4-(3-aminophenyl)-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one

Product 1

HCID 59971445(Z)-N-[3-[2,3-dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]phenyl]-4-(phenylsulfonyl)-2-thiophenesulfonamideYield 36%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of (Z)-4-(3-aminophenyl)-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (60 mg, 0.200 mmol) (from Example 4 supra), Et3N (28 μL , 0.201 mmol), and 4-benzenesulfonylthiophene-2-sulfonyl chloride (64.6 mg, 0.200 mmol) (Lancaster) in 7 mL of 1,2-dimethoxyethane (Fisher Scientific) was heated at reflux for 1 h. The reaction mixture was allowed to cool and then stirred at room temperature for 15 h. The reaction mixture was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 45% ethyl acetate-hexanes elution) provided pure (Z)-N-[3-[2,3-dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]phenyl]-4-(phenylsulfonyl)-2-thiophenesulfonamide (yield: 42 mg, 36%) as a yellow solid (mp 132-134° C.) (solid to gel).

Workup

  1. temperatureat reflux for 1 h
  2. temperatureto cool
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. washFlash chromatography (Merck Silica gel 60, 230-400 mesh, 45% ethyl acetate-hexanes elution)

Sources & evidence

ORD record
ord-61901b7e35b74e589c43f7de1ac0d131
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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