N-methyl-2-pyrrolidone → tert-Butyl 3-(4-(5-(5-chloro-6-isobutylpyridin-3-yl)-1,2,4-oxadiazol-3-yl)-3-methylphenyl)propanoate

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To a solution of 86 mg (0.20 mmol) of tert-butyl 3-(4-(5-(5,6-dichloropyridin-3-yl)-1,2,4-oxadiazol-3-yl)-3-methylphenyl)propanoate (from EXAMPLE 15, Step A), 5.1 mg (0.01 mmol) of bis(tri-tert-butylphosphine)palladium(0), and 200 μL of 1-methyl-2-pyrrolidinone in 5.0 mL of THF was added 475 μL (0.24 mmol) of isobutylzinc bromide (0.5 M in THF). The reaction mixture was refluxed for 4 h, cooled to rt, and filtered through a cake of Celite. The filtrate was concentrated. Chromatography on Biotage 40S cartridge using 7:93 v/v Et2O/hexanes as the eluant afforded 55 mg of the title compound: 1H NMR (500 MHz, CD3OD) δ 0.99 (d, J=6.7, 6H), 1.44 (s, 9H), 2.28 (m, 1H), 2.58 (t, J=7.7, 2H), 2.66 (s, 3H), 2.93-2.97 (m, 4H), 7.18-7.20 (m, 2H), 8.01 (d, J=8.5, 1H), 8.42 (d, J=1.8, 1H), 9.22 (d, J=1.9, 1H).

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