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

HRID 1378531ノート

反応式

HRID 1378531 の反応式
[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]

参加物

8

反応物 6

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-331a156cb16e4c18bce5db10ac9e0fd0
出典データセット
uspto-grants-1997_09
特許番号
US05668152

反応ノート

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