HCID 136413191, compound → HCID 86674960, compound

HRID 1502384Notes

Reaction equation

HRID 1502384 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-a10f9dab30704b1b8f368ed2b09e1d0e
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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