6-Bromoindole → (S)-5-(1H-indol-6-ylethynyl)-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]nicotinamide

HRID 391533Notes

Reaction equation

HRID 391533 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:34]=[C:33]2[C:29]([CH:30]=[CH:31][NH:32]2)=[CH:28][CH:27]=1>>[NH:32]1[C:33]2[C:29](=[CH:28][CH:27]=[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:34]=2)[CH:30]=[CH:31]1

Participants

3

Reactant 2

HCID 6764936-BromoindoleHCID 24953135(S)-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]-5-[(trimethylsilyl)ethynyl]nicotinamide

Product 1

HCID 24954549(S)-5-(1H-indol-6-ylethynyl)-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]nicotinamideYield 17.9%

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 6-bromoindole (90.7 mg, 0.46 mmol) were reacted to give the title compound (30 mg).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-edcf423570494af4b930a913fa3a137f
Source dataset
uspto-grants-2013_02
Patent number
US08383825B2

Reaction notes

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