Diethyl Ether → 3-[1-(1-Ethyl-piperidin-4-yl)-indol-3-yl]-4-(1-methyl-indol-3-yl)-pyrrole-2,5-dione

HRID 2258592노트

반응식

HRID 2258592 반응식
[CH2:1]([N:3]1[CH2:8][CH2:7][CH:6]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10]2)[CH2:5][CH2:4]1)[CH3:2].[C:18](Cl)(=[O:22])[C:19](Cl)=O.Cl.[C:25](=[NH:28])([OH:27])[CH3:26].[C:29](=[NH:32])([O-])[CH3:30].[C:33]1(C)[CH:38]=[CH:37][C:36](S(O)(=O)=O)=[CH:35][CH:34]=1.[CH3:44]COCC>C(Cl)Cl>[CH2:1]([N:3]1[CH2:8][CH2:7][CH:6]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:26]3[C:25](=[O:27])[NH:28][C:18](=[O:22])[C:19]=3[C:30]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[N:32]([CH3:44])[CH:29]=3)=[CH:10]2)[CH2:5][CH2:4]1)[CH3:2]

참가 물질

8

반응물 6

HCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 65578Oxalyl chlorideHCID 21947001AcetimidateHCID 229072501-(1-Ethyl-piperidin-4-yl)-indoleHCID 178465697HCID 178465697, 화합물

생성물 1

HCID 229116023-[1-(1-Ethyl-piperidin-4-yl)-indol-3-yl]-4-(1-methyl-indol-3-yl)-pyrrole-2,5-dione

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

1-(1-ethyl-piperidin-4-yl)-indole (350 mg, 1.53 mmol) was dissolved in ether (6 mL), cooled to 0° C. and oxalyl chloride (0,175 mL, 2 mmol) was slowly added. After 30 minutes, the precipitate which formed was collected and suspended in dry methylene chloride. (10 mL). To this suspension was added isopropyl(1-methyl)indol-3-yl)acetimidate hydrochloride (410 mg, 1.53 mmol), followed by the dropwise addition of isopropyl(1-methyl)indol-3-yl)acetimidate (1.07 mL, 7.65 mmol) in dry methylene chloride (3 mL). After 3.5 hours, p-toluene sulfonic acid (1.16 g, 6.12 mmol) was added in several portions (slightly exothermic reaction) and stirring continued for an additional hour. Title compound was isolated as described in Example 39. Recrystallization from dioxane yielded 180 mg of bright orange crystals (26% yield). M. pt.: >250° C.

후처리

  1. customthe precipitate which formed
  2. customwas collected
  3. waitAfter 3.5 hours
  4. customslightly exothermic reaction) and
  5. waitcontinued for an additional hour

출처 및 근거

ORD 기록
ord-e43ef987ddff4d679e0920221bf8cea2
출처 데이터셋
uspto-grants-1997_08
특허 번호
US05661173

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