5-Bromoisatin → (S)-5-[(2,3-dioxo-2,3-dihydro-1H-indol-5-yl)ethynyl]-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]nicotinamide

HRID 391534Notes

Reaction equation

HRID 391534 reaction equation
[CH3:1][S@:2](=[O:24])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[N:3][C:4](=[O:17])[C:5]1[CH:10]=[C:9]([C:11]#[C:12][Si](C)(C)C)[CH:8]=[N:7][CH:6]=1.Br[C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[NH:31][C:30](=[O:35])[C:29]2=[O:36]>>[O:35]=[C:30]1[C:29](=[O:36])[C:28]2[C:32](=[CH:33][CH:34]=[C:26]([C:12]#[C:11][C:9]3[CH:8]=[N:7][CH:6]=[C:5]([CH:10]=3)[C:4]([N:3]=[S@@:2]([CH3:1])(=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:17])[CH:27]=2)[NH:31]1

Participants

3

Reactant 2

HCID 68895-BromoisatinHCID 24953135(S)-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]-5-[(trimethylsilyl)ethynyl]nicotinamide

Product 1

HCID 24954550(S)-5-[(2,3-dioxo-2,3-dihydro-1H-indol-5-yl)ethynyl]-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]nicotinamideYield 22.2%

Procedure

In a manner similar to that described in Example 443, (S)—N-[methyl(oxo)phenyl-λ6-sulfanylidene]-5-[(trimethylsilyl)ethynyl]nicotinamide (150 mg, 0.42 mmol) and 5-bromoisatin (116 mg, 0.46 mmol) were reacted to give the title compound as a reddish oil (40 mg).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-7319453a349c46ae98f43266761c3258
Source dataset
uspto-grants-2013_02
Patent number
US08383825B2

Reaction notes

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