Tetrahydrofuran → 3-(1H-Indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-1-octadec-9-enoyl-pyrrole-2,5-dione

HRID 427764노트

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HRID 427764 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[C:11](=[O:29])[NH:12][C:13](=[O:28])[C:14]=2[C:15]2[C:23]3[C:18](=[CH:19][C:20]([N+:24]([O-:26])=[O:25])=[CH:21][CH:22]=3)[N:17]([CH3:27])[CH:16]=2)=[CH:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:40](Cl)[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47]/[CH:48]=[CH:49]\[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57].C1C[O:62]CC1>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[C:11](=[O:29])[N:12]([C:40](=[O:62])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH:48]=[CH:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[C:13](=[O:28])[C:14]=2[C:15]2[C:23]3[C:18](=[CH:19][C:20]([N+:24]([O-:26])=[O:25])=[CH:21][CH:22]=3)[N:17]([CH3:27])[CH:16]=2)=[CH:2]1

참가 물질

5

반응물 4

HCID 8028Tetrahydrofuran2회HCID 2733832Lithium HexamethyldisilazideHCID 5367784(9Z)-1-Chloro-9-octadeceneHCID 98864633-(1H-Indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione

생성물 1

HCID 697765353-(1H-Indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-1-octadec-9-enoyl-pyrrole-2,5-dione수율 70%

반응 조건

온도
-60 °C

실험 절차

A solution of 3-(1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione (250 mg, 0.65 mmol), prepared as described in U.S. Ser. No. 09/268,887, was dissolved in THF (15 ml) and cooled to −60° C. To this solution was added lithium bis(trimethylsilyl)amide (0.7 mmol, 0.7 ml, 1.0 M in THF), followed by oleyl chloride (Aldrich) (0.300 g, 1.0 mmol) in THF (5 ml). The resulting mixture was stirred at 0° C. for 1 hr. All solvent was evaporated and the crude material was pre-purified by silica gel chromatography. The resulting products were separated using silica gel chromatography using a gradient of ethyl acetate and hexane. This gave 310 mg of 3-(1H-Indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-1-octadec-9-enoyl-pyrrole-2,5-dione. (Yield 70 %)

후처리

  1. customAll solvent was evaporated
  2. customthe crude material was pre-purified by silica gel chromatography
  3. customThe resulting products were separated

출처 및 근거

ORD 기록
ord-78475b704eec4707b57d9a064829f4ce
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313143B1

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