Methyl chloroacetate → 2-(Chloromethyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridine

HRID 1615617

Reaktionsgleichung

Reaktionsgleichung von HRID 1615617
[NH2:1][N:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([CH3:9])[C:3]1=[NH2+:10].CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[Cl:24][CH2:25][C:26](OC)=O.C(=O)([O-])[O-].[K+].[K+]>CCO>[Cl:24][CH2:25][C:26]1[N:10]=[C:3]2[C:4]([CH3:9])=[CH:5][CH:6]=[C:7]([CH3:8])[N:2]2[N:1]=1

Komponenten

5

Edukt 3

HCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 178425974HCID 178425974, Verbindung

Produkt 1

HCID 666361122-(Chloromethyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridineAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A suspension of 1-amino-3,6-dimethylpyridin-2(1H)-iminium-2,4,6-trimethylbenzenesulfonate (crude product from the previous step, 8.2 mmol), methyl 2-chloroacetate (1.78 g, 16.4 mmol) and potassium carbonate (2.26 g, 16.4 mmol) in EtOH (30 mL) was stirred at 80° C. for 16 h. After cooled to room temperature, the reaction mixture was concentrated and the residue was purified by silica gel column chromatography (eluting with 20% v/v EtOAc in PE) to give the title compound (920 mg, yield 36%, 2 steps). ESI MS: m/z 196, 198 [M+H]+. 1H NMR (400 MHz, CDCl3): δ 7.24 (d, J=7.2 Hz, 1H), 6.77 (d, J=7.2 Hz, 1H), 4.85 (s, 2H), 2.74 (s, 3H), 2.62 (s, 3H).

Aufarbeitung

  1. temperatureAfter cooled to room temperature
  2. concentrationthe reaction mixture was concentrated
  3. customthe residue was purified by silica gel column chromatography (
  4. washeluting with 20% v/v EtOAc in PE)

Quellen und Nachweise

ORD-Eintrag
ord-031301df09e541dba45ef622b70fde53
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765760B2

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