Sodium Hydroxide → 5-(3-(4-cyclopropylpyrimidin-2-yl)-1H-indol-5-yl)-N-(2,2,2-trifluoroethyl)-1,3,4-oxadiazol-2-amine

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Reaction Conditions

Reaction Steps

5-(3-(4-Cyclopropylpyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(2,2,2-trifluoroethyl)-1,3,4-oxadiazol-2-amine (117 mg, 0.211 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 (eluting with 0-8% MeOH in DCM) to give 5-(3-(4-cyclopropylpyrimidin-2-yl)-1H-indol-5-yl)-N-(2,2,2-trifluoroethyl)-1,3,4-oxadiazol-2-amine (19.1 mg, 0.048 mmol, 22.61%) as a pale yellow amorphous solid. MS (ESI, pos. ion) m/z: 401.1 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.95 (br. s., 1H), 9.01 (s, 1H), 8.50-8.59 (m, 2H), 8.27 (d, J=2.3 Hz, 1H), 7.70 (dd, J=8.5, 1.5 Hz, 1H), 7.60 (d, J=8.4 Hz, 1H), 7.16 (d, J=5.3 Hz, 1H), 4.05-4.21 (m, 2H), 2.08-2.20 (m, 1H), 1.20-1.29 (m, 2H), 1.07-1.16 (m, 2H).

Provenance & Evidence