Reaktion #358658

Reaktionsgleichung

2-(Bromomethyl)pyridine hydrobromide

Sodium hydride

2-methyl-4-(2-methyl-1H-imidazol-4-ylethynyl)-pyridine

water

→

desired compound

4-[1-(Pyridin-2-ylmethyl)-2-methyl-1H-imidazol-4-ylethynyl]-2-methyl-pyridine

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued overnight
3. 3
   Extraktionextracted three times with ethyl acetate (70 mL each)
4. 4
   TrocknenThe combined organic extracts were dried with sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe crude product was purified by flash chromatography on silica gel (dichloromethane/methanol 100:0→90:10 gradient)
8. 8
   workup.ADDITIONa mixture of two regioisomers
9. 9
   Sonstigewas obtained
10. 10
    SonstigeThis mixture could be separated by crystallization from diethylether

Vorschrift

Sodium hydride (69 mg, 55%, 1.59 mmol) was suspended in 2 mL dry THF. A solution of 2-methyl-4-(2-methyl-1H-imidazol-4-ylethynyl)-pyridine (95 mg, 0.48 mmol) in 8 mL dry THF was added and the reaction mixture was stirred at room temperature for 30 min. 2-(Bromomethyl)pyridine hydrobromide (162 mg, 0.63 mmol) was added and stirring was continued overnight. The reaction mixture was poured into 70 mL water and extracted three times with ethyl acetate (70 mL each). The combined organic extracts were dried with sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel (dichloromethane/methanol 100:0→90:10 gradient) and a mixture of two regioisomers was obtained. This mixture could be separated by crystallization from diethylether and the desired compound was obtained as a white solid (35 mg, 25%), MS: m/e=289.1 (M+H30).

Quelle