Reaction #68585

Reaction equation

NaOH

tert-butyl 2-(3-(2-methoxyethoxy)quinolin-6-yl)acetate

1-(6-phenylpyridazin-3-yl)hydrazine

HYDROCHLORIC ACID

→

desired product

3-(2-methoxyethoxy)-6-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinoline

Solvents

water

Conditions

Workup

1. 1
   OtherThe vial was sealed
2. 2
   Filtrationthe precipitate was collected via filtration
3. 3
   workup.DISSOLUTIONwas dissolved in DCM
4. 4
   WashThe organic was washed with water
5. 5
   Dryingdried over MgSO4
6. 6
   Otherremoved solvent in vacuo
7. 7
   OtherThe crude product was purified

Procedure

To a 5 ml CEM microwave tube was added tert-butyl 2-(3-(2-methoxyethoxy)quinolin-6-yl)acetate (0.080 g, 0.25 mmol), 1-(6-phenylpyridazin-3-yl)hydrazine (0.094 g, 0.50 mmol), HYDROCHLORIC ACID (0.063 ml, 0.76 mmol), and water (0.2 mL) as solvent. The vial was sealed and first heated at 90° C. for 30 min then placed into CEM microwave for 15 min. at 140° C., with 100 Watts of power via Powermax. The reaction mixture was adjusted the pH to 7 by adding 5 N NaOH and the precipitate was collected via filtration. The brown ppt. was dissolved in DCM. The organic was washed with water, dried over MgSO4, and removed solvent in vacuo. The crude product was purified using SiO2 chromatography (Teledyne Isco RediSep®, P/N 68-2203-026, 12 g SiO2, DCM:EtOAc:MeOH=60%:37%:3%, Flow=30 mL/min) to afford the desired product as light yellowish solid. MS m/z: 412.3 (M+H). Calc'd. for C24H21N5O2−411.45.

Source