Tetrabutylammonium Fluoride → 5-(3-chloro-4-methoxyphenyl)-3-(1H-indol-5-yl)-1,2,4-oxadiazole

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Reaction Steps

A suspension of the product of Step D (0.4 g; 1.16 mmol) and 1M TBAF in THF (0.5 ml) in anhydrous toluene (10 ml) was refluxed for 3 h under N2, cooled to room temperature and solvents were removed under reduced pressure. The residue was washed with H2O (5 ml) and the solid was purified by FCC (SiO2; CH2Cl2) to give the title compound (0.35 g; 92%) as colourless solid. 1H-NMR (CDCl3) 4.0 (s, 3H); 6.66 (m, 1H); 7.05 (d, 1H, J=8.7 Hz); 7.27 (m, 1H); 7.49 (d, 1H, J=8.7 Hz); 7.97-8.01 (m, 1H); 8.1-8.13 (m, 1H); 8.27 (d, 1H, J=2.1 Hz); 8.3 (broad s, 1H); 8.48 (m, 1H).

Provenance & Evidence