Benzoyl Peroxide → 5-Chlorothieno[3,2-b]pyridine-3-carbaldehyde

HRID 1773508Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1773508
[Cl:1][C:2]1[N:7]=[C:6]2[C:8]([CH3:11])=[CH:9][S:10][C:5]2=[CH:4][CH:3]=1.BrN1C(=[O:18])CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]2[C:8]([CH:11]=[O:18])=[CH:9][S:10][C:5]2=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 580562155-Chloro-3-methylthieno[3,2-B]pyridine

Produkt 1

HCID 14762645-Chlorothieno[3,2-b]pyridine-3-carbaldehydeAusbeute 28,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 5-chloro-3-methyl-thieno[3,2-b]pyridine (0.5 g, 2.7 mmol), N-bromosuccinimide (0.48 g, 2.7 mmol) and benzoyl peroxide (50 mg) in carbon tetrachloride (3 mL) was heated at 100° C. in a microwave reactor for 15 minutes. The supernatant was decanted and evaporated under reduced pressure, the residue was suspended in toluene (3 mL) and pyridine-N-oxide (0.5 g) was added, followed by sodium bicarbonate (0.4 g) and diisopropylethylamine (3 drops). The reaction mixture was heated at 150° C. in a microwave reactor for 5 minutes, was then diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (EtOAc/hexane, 20/80) to give 150 mg of 5-chloro-thieno[3,2-b]pyridine-3-carbaldehyde.

Aufarbeitung

  1. customThe supernatant was decanted
  2. customevaporated under reduced pressure
  3. additionpyridine-N-oxide (0.5 g) was added
  4. temperatureThe reaction mixture was heated at 150° C. in a microwave reactor for 5 minutes
  5. additionwas then diluted with ethyl acetate
  6. washwashed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe crude residue was purified by flash chromatography (EtOAc/hexane, 20/80)

Quellen und Nachweise

ORD-Eintrag
ord-3ae575843b5044ba84e084ac97166340
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09255110B2

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