1,3-Dichloroacetone → 2-(chloromethyl)-5-methylimidazo[1,2-a]pyridine

HRID 1798717Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1798717
[Cl:1][CH2:2][C:3]([CH2:5]Cl)=O.[CH3:7][C:8]1[N:13]=[C:12]([NH2:14])[CH:11]=[CH:10][CH:9]=1>C(#N)C>[Cl:1][CH2:2][C:3]1[N:14]=[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([CH3:7])[N:13]2[CH:5]=1

Komponenten

4

Edukt 2

HCID 107931,3-DichloroacetoneHCID 157652-Amino-6-methylpyridine

Produkt 1

HCID 9576122-(chloromethyl)-5-methylimidazo[1,2-a]pyridineAusbeute 70,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1,3-Dichloroacetone (17.6 g, 138.3 mmol) was added to a solution of 6-methylpyridin-2-amine (10 g, 92.5 mmol) in acetonitrile (200 ml). The mixture was heated at reflux for 14 h (the reaction was monitored by TLC). The mixture was concentrated under reduced pressure, the residue was diluted with water, and the pH was adjusted to 7.5 with sodium bicarbonate solution. The mixture was extracted with EtOAc, the combined organics were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography using 10% ethyl acetate in n-hexane and silica gel (230-400 mesh) to afford 2-(chloromethyl)-5-methylimidazo[1,2-a]pyridine (7.0 g, 70.7%) as a pale yellow solid. 1H NMR: 200 MHz, CDCl3: δ 8.15 (s, 1H), 7.6 (dd, 2H), 7.1 (t, 1H), 6.8 (t, 1H), 4.95 (s, 2H), 2.6 (s, 3H). MS: [M+H]+: m/z=181.5.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 14 h (the reaction
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additionthe residue was diluted with water
  5. extractionThe mixture was extracted with EtOAc
  6. dry with materialthe combined organics were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e4e15195714f4f06bbf40851455bbc48
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343973B2

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