Réaction #77548

Équation de réaction

1-[(6-bromohexyl)oxy]-4-fluorobenzene

DMF

[5-methyl-1-(4-pyridyl)tetrahydro-1H-2-imidazolyliden]amino methanenitrile

sodium hydride

DMF

→

Compound 13

1-[6-(4-fluorophenoxy)hexyl]-4-methyl-3-(4-pyridyl)-2-imidazolidinone

Conditions de réaction

Traitement

1. 1
   TempératureThe resulting mixture was heated to 80° C.
2. 2
   workup.STIRRINGstirred overnight (16 hours)
3. 3
   AutreThe solvent was removed under reduced pressure
4. 4
   Autrethe crude residue was purified by column chromatography
5. 5
   Lavageeluting with 15% methanol in ethyl acetate

Mode opératoire

To a solution of [5-methyl-1-(4-pyridyl)tetrahydro-1H-2-imidazolyliden]amino methanenitrile (60 mg, 0.30 mmol) in DMF (5 mL) at 0° C. was added sodium hydride (19 mg, 0.60 mmol, 75% in mineral oil) in one portion. The mixture was stirred at room temperature for 20 min followed by addition of 1-[(6-bromohexyl)oxy]-4-fluorobenzene (123 mg, 0.45 mmol) dissolved in DMF (3 ml) drop by drop. The resulting mixture was heated to 80° C. and stirred overnight (16 hours). The solvent was removed under reduced pressure and the crude residue was purified by column chromatography eluting with 15% methanol in ethyl acetate to afford the product (i.e., Compound 13) as a white solid (44 mg, 37%).

Source