Tetrabutylammonium Fluoride → N-Benzyl-2,3-dibromomaleimide

HRID 1724828Notes

Reaction equation

HRID 1724828 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]3[N:14]=[C:15]([C:17]4[CH:22]=[CH:21][C:20]5[NH:23][C:24]([NH:32][C:19]=5[CH:18]=4)=[C:25]4[CH:31]=[CH:30][C:28](=[O:29])[CH:27]=[CH:26]4)[NH:16][C:10]=3[CH:9]=2)[CH2:4][CH2:3]1.[Si]([N:40]1[C:44](=[O:45])[C:43]([Br:46])=[C:42]([Br:47])[C:41]1=[O:48])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]3[N:14]=[C:15]([C:17]4[CH:22]=[CH:21][C:20]5[NH:23][C:24]([NH:32][C:19]=5[CH:18]=4)=[C:25]4[CH:31]=[CH:30][C:28](=[O:29])[CH:27]=[CH:26]4)[NH:16][C:10]=3[CH:9]=2)[CH2:4][CH2:3]1.[CH2:15]([N:40]1[C:41](=[O:48])[C:42]([Br:47])=[C:43]([Br:46])[C:44]1=[O:45])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 106904181H-Pyrrole-2,5-dione, 3,4-dibromo-1-[(1,1-dimethylethyl)dimethylsilyl]-HCID 178480630HCID 178480630, compound

Product 2

HCID 3457221N-Benzyl-2,3-dibromomaleimideHCID 178480630HCID 178480630, compound

Procedure

As depicted in Scheme I, bisbenzimidazolomaleimide (3) was synthesized in an economical fashion from readily available precursors in two steps by condensing deprotonated bisbenzimidazole (4) with N-TBDMS-2,3-dibromomaleimide (6a) followed by deprotection with TBAF to afford 3. Lactam 4 was obtained by condensing deprotonated bisbenzimidazole 5 with N-benzyl-2,3-dibromomaleimide 7, yielding 9, followed by a reduction and deprotection sequence, as shown in Scheme 1.

Workup

  1. customto afford 3

Sources & evidence

ORD record
ord-ec42b8b5b0204a41b27017aab36fb7aa
Source dataset
uspto-grants-2009_02
Patent number
US07488817B2

Reaction notes

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