1,2-Dichloroethane → 2,3-dimethoxy-benzoic acid 1-{3-[4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-indol-1-yl}-ethyl ester

HRID 427771Notes

Reaction equation

HRID 427771 reaction equation
[OH:1][CH:2]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]2[C:14](=[O:32])[NH:15][C:16](=[O:31])[C:17]=2[C:18]2[C:26]3[C:21](=[CH:22][C:23]([N+:27]([O-:29])=[O:28])=[CH:24][CH:25]=3)[N:20]([CH3:30])[CH:19]=2)=[CH:5]1)[CH3:3].C(Cl)CCl.CN(C1C=CC=CN=1)C.[CH3:46][O:47][C:48]1[C:56]([O:57][CH3:58])=[CH:55][CH:54]=[CH:53][C:49]=1[C:50](O)=[O:51]>C(Cl)Cl>[CH3:30][N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=2)[C:18]([C:17]2[C:16](=[O:31])[NH:15][C:14](=[O:32])[C:13]=2[C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:4]([CH:2]([O:1][C:50](=[O:51])[C:49]3[CH:53]=[CH:54][CH:55]=[C:56]([O:57][CH3:58])[C:48]=3[O:47][CH3:46])[CH3:3])[CH:5]=2)=[CH:19]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 152042,3-Dimethoxybenzoic acidHCID 218852-DimethylaminopyridineHCID 183577193-[1-(1-hydroxy-ethyl)-1H-indol-3-yl]-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione

Product 1

HCID 102106692,3-dimethoxy-benzoic acid 1-{3-[4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-indol-1-yl}-ethyl esterYield 51.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[1-(1-hydroxy-ethyl)-1H-indol-3-yl]-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione (165.3 mg, 0.678 mmol) (from step d) above), EDC.HCL (284.5 mg, 1.484 mmol), and dimethylaminopyridine (185.5 mg, 1.58 mmol) in 20 mL of CH2Cl2 was added 2,3-dimethoxybenzoic acid (287.4 mg, 0.668 mmol). The solution was stirred at room temperature for 0.5 hour, washed with saturated NaHCO3, brine, dried over magnesium sulfate, and evaporated. The residue was purified by flash chromatography using EtOAc/hexanes to give 203 mg of 2,3-dimethoxy-benzoic acid 1-{3-[4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-indol-1-yl}-ethyl ester. (Yield 50%).

Workup

  1. washwashed with saturated NaHCO3, brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-b3281f582c2c456daf9c1fac32b4f41d
Source dataset
uspto-grants-2001_11
Patent number
US06313143B1

Reaction notes

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