HCID 136413191, compound → HCID 86674960, compound

HRID 468867Notes

Reaction equation

HRID 468867 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](=[N:10][OH:11])[CH3:9])[C:5]([C:12]#[C:13][C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[CH3:21])=[CH:4][N:3]=1>C(Cl)(Cl)Cl.[N+]([O-])([O-])=O.[Ag+]>[Cl:1][C:2]1[CH:7]=[C:6]2[C:5]([CH:12]=[C:13]([C:14]3[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=3[CH3:21])[N+:10]([O-:11])=[C:8]2[CH3:9])=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 136413191HCID 136413191, compound

Product 1

HCID 86674960HCID 86674960, compoundYield 57.8%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-(2-chloro-5-((5-fluoro-2-methylphenyl)ethynyl)pyridin-4-yl)ethanone oxime (700 mg, 2.0 mmol) and silver nitrate (−10 wt. % on silica gel, +230 mesh, 825 mg, 0.5 mmol) in chloroform (12 mL) was heated at 60° C. for 1 hour. The cooled reaction mixture was treated with silica gel (2 g), concentrated in vacuo, and purified by flash chromatography (silica, 12 g, ISCO, 0-90% ethyl acetate in heptane) to afford the title compound as pale yellow solid (350 mg, 50% over two steps), which was used in the next step without further purification.

Workup

  1. customThe cooled reaction mixture
  2. additionwas treated with silica gel (2 g)
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography (silica, 12 g, ISCO, 0-90% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-6bd4695b169a4a3ba274eb3d81787b3d
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

Loading…