Trichloroacetonitrile → 3-[3-(2-{[tert-Butyl(diphenyl)silyl]oxy}ethyl)-1,2,4-oxadiazol-5-yl]-6-chloro-2-methylpyridine

Participants

Reaction Conditions

Reaction Steps

6-Chloro-2-methylnicotinic acid (Example 425, Step 1) (150 mg, 0.87 mmol) trichloroacetonitrile (0.13 ml, 1.31 mmol) and solid supported triphenylphosphine on polystyrene (1.88 mmol/g, 1.5 g, 2.62 mmol) were taken up in tetrahydrofuran (10.9 ml). The mixture was heated in the microwave at 100° C. for 5 minutes and cooled to room temperature. (1Z)-3-{[tert-Butyl(diphenyl)silyl]oxy}-N′-hydroxypropanimidamide (329 mg, 0.96 mmol), THF (5 mL), and N-ethyl-N-isopropylpropan-2-amine (0.15 ml, 0.87 mmol) were added. The resulting mixture was heated in the microwave at 150° C. for 15 minutes, cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and purified via silica gel chromatography (0-35% ethyl acetate in hexane) to afford the title compound.

Provenance & Evidence