2-Benzoxazolinone, 5-bromo- → (S)-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]-5-[(2-oxo-2,3-dihydro-1,3-benzoxazol-5-yl)ethynyl]nicotinamide

HRID 1099630Notes

Reaction equation

HRID 1099630 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]=[CH:28][C:29]2[O:33][C:32](=[O:34])[NH:31][C:30]=2[CH:35]=1>>[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][C:26]2[CH:27]=[CH:28][C:29]3[O:33][C:32](=[O:34])[NH:31][C:30]=3[CH:35]=2)[CH:8]=[N:7][CH:6]=1

Participants

3

Reactant 2

HCID 268532-Benzoxazolinone, 5-bromo-HCID 24953135(S)-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]-5-[(trimethylsilyl)ethynyl]nicotinamide

Product 1

HCID 24954922(S)-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]-5-[(2-oxo-2,3-dihydro-1,3-benzoxazol-5-yl)ethynyl]nicotinamideYield 40.5%

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-bromo-2-benzoxazolinone (102 mg, 0.46 mmol) were reacted to give the title compound as light yellow solid (71 mg).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-7475692cb93d4788ba99373ae63bba93
Source dataset
uspto-grants-2012_03
Patent number
US08143410B2

Reaction notes

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