Sodium Hydroxide → 2-cyclopropyl-5-(3-(4-cyclopropylpyrimidin-2-yl)-1H-indol-5-yl)-1,3,4-oxadiazole

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Reaction Conditions

Reaction Steps

2-Cyclopropyl-5-(3-(4-cyclopropylpyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazole (78.6 mg, 0.158 mmol) in a 5 mL glass microwave tube, was suspended in dioxane (1.5 mL). The suspension was treated with NaOH 1.000 n (2 mL, 2.000 mmol) (Fluka Analytical). The tube was sealed and the contents were stirred and heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 100° C. for 10 min. The mixture was diluted with H2O (10 mL) and extracted with EtOAc (2×25 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The crude material was purified by flash chromatography (0-10% MeOH in DCM) to give 2-cyclopropyl-5-(3-(4-cyclopropylpyrimidin-2-yl)-1H-indol-5-yl)-1,3,4-oxadiazole (19.2 mg, 0.056 mmol, 35.4%) as a pale yellow amorphous solid. MS (ESI, pos. ion) m/z: 344.0 (M+1). 1H NMR (400 MHz, DMSO-d6) ppm 11.99 (br. s., 1H), 9.10 (s, 1H), 8.56 (d, J=5.3 Hz, 1H), 8.28 (s, 1H), 7.77-7.84 (m, 1H), 7.62 (d, J=8.6 Hz, 1H), 7.20 (d, J=5.1 Hz, 1H), 2.29-2.38 (m, 1H), 2.09-2.20 (m, 1H), 1.12-1.33 (m, 8H).

Provenance & Evidence