Dimethylformamide → HCID 68997573, compound

Participants

Reaction Steps

(E)-3-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}[1,2,4]oxadiazole-5-carboxylic acid (14 mg, 0.04 mmol) obtained in Step 2 of Example 175 was dissolved in methylene chloride (1.0 mL), and thionyl chloride (5 μL, 239-0.06 mmol) and DMF (few drops) were added thereto, followed by stirring for 30 minutes. Then the mixture was concentrated and the residue was dissolved in dioxane (1.0 mL). Sodium borohydride (16 mg, 0.42 mmol) was added to the solution and the mixture was stirred at room temperature for 1 hour. Water was added to stop the reaction and the reaction mixture was extracted with ethyl acetate. The organic layer was concentrated and the residue was purified by preparative thin-layer chromatography (chloroform/acetone=4/1) to obtain Compound 179 (3.5 mg, 26%).

Provenance & Evidence