2-Chloro-5-iodopyridine → (S)-5-[(6-chloropyridin-3-yl)ethynyl]-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]nicotinamide

HRID 391535Notes

Reaction equation

HRID 391535 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.[Cl:25][C:26]1[CH:31]=[CH:30][C:29](I)=[CH:28][N:27]=1>>[Cl:25][C:26]1[N:27]=[CH:28][C:29]([C:12]#[C:11][C:9]2[CH:8]=[N:7][CH:6]=[C:5]([CH:10]=2)[C:4]([N:3]=[S@@:2]([CH3:1])(=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:17])=[CH:30][CH:31]=1

Participants

3

Reactant 2

HCID 43971762-Chloro-5-iodopyridineHCID 24953135(S)-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]-5-[(trimethylsilyl)ethynyl]nicotinamide

Product 1

HCID 24954920(S)-5-[(6-chloropyridin-3-yl)ethynyl]-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]nicotinamideYield 90.2%

Procedure

In a manner similar to that described in Example 443, (S)—N-[methyl(oxo)phenyl-λ6-sulfanylidene]-5-[(trimethylsilyl)ethynyl]nicotinamide (250 mg, 0.70 mmol) and 2-chloro-5-iodopyridine (173 mg, 0.70 mmol) were reacted to give the title compound as white solid (250 mg).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-6f5932d038374fc38d75ddd6d73dfdbb
Source dataset
uspto-grants-2013_02
Patent number
US08383825B2

Reaction notes

Loading…