Benzene → But-2-enedioic Acid Mono-[3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl] Ester

HRID 411770

Reaction equation

HRID 411770 reaction equation
[OH:1][CH2:2][N:3]1[C:7](=[O:8])[C:6]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[CH:15][CH:16]=3)[N:11]([CH3:21])[CH:10]=2)=[C:5]([C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]([CH3:31])[CH:23]=2)[C:4]1=[O:32].C1C=CC=CC=1.[C:39](Cl)(=[O:45])/[CH:40]=[CH:41]/[C:42](Cl)=[O:43].C(N(C(C)C)CC)(C)C.[OH2:56]>C(Cl)Cl.CC(C)=O>[CH3:31][N:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22]([C:5]2[C:4](=[O:32])[N:3]([CH2:2][O:1][C:39](=[O:45])[CH:40]=[CH:41][C:42]([OH:56])=[O:43])[C:7](=[O:8])[C:6]=2[C:9]2[C:17]3[C:12](=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[CH:15][CH:16]=3)[N:11]([CH3:21])[CH:10]=2)=[CH:23]1

Participants

8

Reactant 5

HCID 241BenzeneHCID 962WaterHCID 81531DiisopropylethylamineHCID 5325504Fumaryl chlorideHCID 98673381-hydroxymethyl-3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione

Product 1

HCID 69945086But-2-enedioic Acid Mono-[3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl] EsterYield 60%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-Hydroxymethyl-3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione, prepared as in example 1a, in 1:4 CH2Cl2:benzene, were added a large excess of fumaryl chloride and excess diisopropylethylamine. The reaction was stirred at room temperature for 20 min. Acetone and water were, added. The reaction mixture was diluted with CH2Cl2, washed with water, cold saturated NaHCO3, water and dried over Na2SO4. The resulting but-2-enedioic acid mono-[3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl] ester was purified by flash chromatography (yield 60%).

Workup

  1. additionadded
  2. washwashed with water, cold saturated NaHCO3, water
  3. dry with materialdried over Na2SO4
  4. customThe resulting but-2-enedioic acid mono-[3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl] ester was purified by flash chromatography (yield 60%)

Sources & evidence

ORD record
ord-73a3beae291a44caba9931cc95d6bb7f
Source dataset
uspto-grants-2003_05
Patent number
US06559164B1

Linked notes

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