Benzene, 1-bromo-2-(trifluoromethyl)- → 5-(3,4-Diethoxyphenyl)-3-(4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl)-1,2,4-oxadiazole

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Reaction Steps

When the product of Step B was substituted for 2-trifluoromethyl-bromobenzene and 3,6-dihydro-2H-pyridine-1-tert-butoxycarbonyl-4-boronic acid was substituted for 4-carbaldehyde boronic acid in Example 36 Step A, the similar process gave the title compound in 57% yield. This (0.085 g) was dissolved in anhydrous CH2Cl2 (2 ml) and CF3CO2H (0.5 ml) was added to it. The mixture was stirred for 3 h, then the solvent was evaporated to dryness. The residue was purified by FCC (SiO2) to give the title compound (0.063 g, 93%), as a colourless solid. 1H-NMR (CDCl3) 1.47-1.52 (m, 6H); 2.72 (m, 2H); 3.33-3.29 (m, 2H); 3.75 (m, 2H); 4.14-4.24 (m, 4H); 6.2 (s, 1H); 6.97 (d, 1H, J=8.4 Hz); 7.64-7.68 (m, 3H); 7.78 (d, 1H, J=8.42); 8.24 (d, 2H, J=8.19 Hz).

Provenance & Evidence