Sodium Hydroxide → 2-(3-(6-cyclopropylpyrazin-2-yl)-1H-indol-5-yl)-5-phenyl-1,3,4-thiadiazole

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Reaction Conditions

Reaction Steps

In a 20 mL glass microwave tube 2-(3-(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-5-phenyl-1,3,4-thiadiazole (190 mg, 0.346 mmol) was treated with dioxane (2.5 mL) and 1N NaOH (0.75 mL) and heated in the microwave to 100° C. for 10 min. The mixture was treated with H2O, extracted with EtOAc (2×15 mL), washed with brine, dried over MgSO4, filtered and concentrated affording 2-(3-(6-cyclopropylpyrazin-2-yl)-1H-indol-5-yl)-5-phenyl-1,3,4-thiadiazole (89 mg, 65%) as a yellow amorphous solid. (ESI, pos. ion) m/z: 396.0 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.06 (1H, br. s.), 9.13 (1H, s), 8.96 (1H, s), 8.43 (1H, d, J=2.5 Hz), 8.40 (1H, s), 7.99-8.08 (2H, m), 7.89-7.96 (1H, m), 7.58-7.69 (4H, m), 2.23-2.32 (1H, m), 1.17-1.30 (4H, m).

Provenance & Evidence