Water → 2-(3-(6-isopropoxypyridin-2-yl)-1H-indol-5-yl)-5-methyl-1,3,4-oxadiazole

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Reaction Conditions

Reaction Steps

2-(3-(6-Isopropoxypyridin-2-yl)-1-tosyl-1H-indol-5-yl)-5-methyl-1,3,4-oxadiazole (214 mg, 0.438 mmol) in a round bottomed flask was dissolved in MeOH (1.500 mL) and THF (3.0 mL). Cesium carbonate (428 mg, 1.314 mmol) (Aldrich) was added, the flask was fitted with a reflux condenser and the contents of the flask were heated at 45° C. for 15 min. H2O (30 mL) was added and the mixture was extracted with EtOAc (2×75 mL). The combined organic layers were dried, filtered and concentrated. The residue was purified with RP-HPLC (10-90% MeCN in H2O with 0.01% TFA as additive) to give 2-(3-(6-isopropoxypyridin-2-yl)-1H-indol-5-yl)-5-methyl-1,3,4-oxadiazole (33.6 mg, 11.1%). MS (ESI, pos. ion) m/z 335.1 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 11.89 (br. s., 1H), 9.20-9.29 (m, 1H), 8.25 (d, J=2.5 Hz, 1H), 7.82 (dd, J=8.5, 1.7 Hz, 1H), 7.57-7.72 (m, 2H), 7.46 (d, J=7.4 Hz, 1H), 6.53 (d, J=8.0 Hz, 1H), 5.58 (dt, J=12.3, 6.2 Hz, 1H), 2.59 (s, 3H), 1.47 (d, J=6.1 Hz, 6H).

Provenance & Evidence