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 427771노트

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HRID 427771 반응식
[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

참가 물질

6

반응물 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

생성물 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 ester수율 51.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-b3281f582c2c456daf9c1fac32b4f41d
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313143B1

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