Maleimide → 9-(Benzyloxy)-4-[2-(2-methoxyethoxy)phenyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11147Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][CH2:27][CH2:28][O:29][CH3:30])=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:31]1(=[O:37])[NH:35][C:34](=[O:36])[CH:33]=[CH:32]1>>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:15]2[NH:14][C:13]3[CH:18]=[C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[O:26][CH2:27][CH2:28][O:29][CH3:30])[C:33]4[C:34](=[O:36])[NH:35][C:31](=[O:37])[C:32]=4[C:12]=3[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 10935Maleimide

HCID 21980709HCID 21980709, compound

Product 1

HCID 219808119-(Benzyloxy)-4-[2-(2-methoxyethoxy)phenyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneYield 46%

Procedure

Reaction of (852) with maleimide using the procedure described in method 4a gave the adduct (CIII; Ar=2-(2-methoxyethoxy)phenyl, R10═H (853), which was used without further purification. Aromatisation of (853) with MnO2 using the procedure described in example 79 gave (854) (46%) as an orange solid, mp 157–159° C., which was used without further purification.

Workup

customgave the adduct (CIII
customAr=2-(2-methoxyethoxy)phenyl, R10═H (853), which was used without further purification

Sources & evidence

ORD record: ord-79ef9e4d9baf47909d82b5c863d6a907
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094798B1

Reaction notes

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