Pyridinium hydrochloride → 4-{5-Chloro-2-[(trimethylsilyl)ethynyl]phenyl}pyridin-2(1H)-one

HRID 56638

Reaction equation

HRID 56638 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:16]#[C:17][Si:18]([CH3:21])([CH3:20])[CH3:19])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([O:14]C)[CH:9]=2)[CH:7]=1.Cl.[NH+]1C=CC=CC=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:16]#[C:17][Si:18]([CH3:19])([CH3:21])[CH3:20])=[C:6]([C:8]2[CH:13]=[CH:12][NH:11][C:10](=[O:14])[CH:9]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 21584435Pyridinium hydrochlorideHCID 1233889294-{5-Chloro-2-[(trimethylsilyl)ethynyl]phenyl}-2-methoxypyridine

Product 1

HCID 1238372604-{5-Chloro-2-[(trimethylsilyl)ethynyl]phenyl}pyridin-2(1H)-one

Procedure

550 mg (purity 41%, 0.71 mmol) of 4-{5-chloro-2-[(trimethylsilyl)ethynyl]phenyl}-2-methoxypyridine and 20 eq. of pyridinium hydrochloride were reacted according to General Method 3A. The reaction mixture was concentrated under reduced pressure and water was added to the residue. After addition of ethyl acetate and phase separation, the organic phase was washed once with water, dried (sodium sulphate), filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel 60, cyclohexane/ethyl acetate and dichloromethane/methanol mixtures). Yield: 141 mg (purity 91%, 59% of theory)

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and water
  2. additionwas added to the residue
  3. additionAfter addition of ethyl acetate and phase separation
  4. washthe organic phase was washed once with water
  5. dry with materialdried (sodium sulphate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by flash chromatography (silica gel 60, cyclohexane/ethyl acetate and dichloromethane/methanol mixtures)

Sources & evidence

ORD record
ord-170c206dd1f84412a7fb90f74ab54455
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Linked notes

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