Maleimide → 6-(3-{[Tert-butyl(dimethyl)silyl]oxy}propyl)-9-methoxy-4-(2-methoxyphenyl)-4,5,6,10c-tetrahydropyrrolo[3,4-c]carbazole-1,3(2h, 3ah)-dione

HRID 11049

Reaction equation

HRID 11049 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[CH:14]=[C:13]1[CH:23]=[CH:24][C:25]1[C:30]([O:31][CH3:32])=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:33])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:34]1(=[O:40])[NH:38][C:37](=[O:39])[CH:36]=[CH:35]1>>[Cl:33][C:26]1[CH:27]=[CH:28][CH:29]=[C:30]([O:31][CH3:32])[C:25]=1[CH:24]1[CH:36]2[C:37](=[O:39])[NH:38][C:34](=[O:40])[CH:35]2[C:14]2[C:15]3[CH:16]=[C:17]([O:21][CH3:22])[CH:18]=[CH:19][C:20]=3[NH:12][C:13]=2[CH2:23]1.[Si:1]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:13]2[CH2:23][CH:24]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=3[O:31][CH3:32])[CH:36]3[C:37](=[O:39])[NH:38][C:34](=[O:40])[CH:35]3[C:14]=2[C:15]2[CH:16]=[C:17]([O:21][CH3:22])[CH:18]=[CH:19][C:20]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 10935MaleimideHCID 867601951-(3-{[tert-Butyl(dimethyl)silyl]oxy}propyl)-2-[2-(2-chloro-6-methoxyphenyl)ethenyl]-5-methoxy-1H-indole

Product 2

HCID 867601946-(3-{[Tert-butyl(dimethyl)silyl]oxy}propyl)-9-methoxy-4-(2-methoxyphenyl)-4,5,6,10c-tetrahydropyrrolo[3,4-c]carbazole-1,3(2h, 3ah)-dioneHCID 1317259044-(2-chloro-6-methoxyphenyl)-9-methoxy-4,5,6,10c-tetrahydropyrrolo[3,4-c]carbazole-1,3(2H,3aH)-dione

Procedure

The reaction of 1-(3-{[tert-Butyl(dimethyl)silyl]oxy}propyl)-2-[2-(2-chloro-6-methoxyphenyl)ethenyl]-5-methoxy-1H-indole (III; Ar=2-chloro-6-methoxyphenyl, R10═CH2CH2CH2OSiMe2t-Bu) (103) prepared as described in example 56 with maleimide using the procedure described in example 68 gave 6-(3-[tert-Butyl(dimethyl)silyl]oxy}propyl)-4-(2-chloro-6-methoxyphenyl)-9-methoxy-4,5,6,10c-tetrahydropyrrolo[3,4-c]carbazole-1,3(2H,3aH)-dione (IV; Ar=2-chloro-6-methoxyphenyl, R10═CH2CH2CH2OSiMe2t-Bu) (104) in a 77% yield as a cream powder, which was used without further purification.

Sources & evidence

ORD record
ord-f0c7b50e2fa14884897237926ba5e44f
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Linked notes

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