HCID 86657320, compound → HCID 58418018, compound
Reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[CH:14]=3)[N:9]=2)[CH:5]=[C:4]([CH3:20])[N:3]=1>O1CCOCC1.O>[CH2:5]([C:2]1[CH:7]=[C:6]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[CH:14]=3)[N:9]=2)[CH:5]=[C:4]([CH3:20])[N:3]=1)[CH:6]([CH3:8])[CH3:7]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 2-chloro-4-[3-(2-methyl-4-pyridinyl)-[1,2,4]oxadiazol-5-yl]-6-methyl-pyridine (200 mg, 0.698 mmol) in dioxane (10 mL), Pd(dppf) (11 mg, 14 μmol) and isobutyl zink bromide (2.8 mL, 0.5 M in THF) is added. The mixture is stirred at 80° C. for 3 h before another portion of isobutyl zink bromide (2.8 mL) is added. Stirring is continued at 80° C. for 72 h. The mixture is cooled to rt, diluted with water and extracted with EA. The org. extract is concentrated and the crude product is purified by prep. HPLC to give 2-isobutyl-4-[3-(2-methyl-4-pyridinyl)-[1,2,4]oxadiazol-5-yl]-6-methyl-pyridine (22 mg) as a beige solid; LC-MS: tR=0.71 min, [M+1]+=309.12.