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

HRID 1378531Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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customwas collected
waitAfter 3.5 hours
customslightly exothermic reaction) and
waitcontinued for an additional hour

Sources & evidence

ORD record: ord-331a156cb16e4c18bce5db10ac9e0fd0
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05668152

Reaction notes

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