Reacción #721386

Ecuación de reacción

2-cyclopropyl-5-(3-(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazole

NaOH

→

2-cyclopropyl-5-(3-(6-cyclopropylpyrazin-2-yl)-1H-indol-5-yl)-1,3,4-oxadiazole

Rendimiento 50.0%

Disolventes

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otropartitioned between DCM (50 mL) and H2O (30 mL)
2. 2
   OtroThe organic layer was separated
3. 3
   Extracciónthe aqueous layer was extracted with DCM (30 mL)
4. 4
   SecadoThe combined organic extracts were dried over sodium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroChromatographic purification of the residue (silica gel, 0-100% (10% MeOH-EtOAc)/Hex)

Procedimiento

A yellow solution of 2-cyclopropyl-5-(3-(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazole (206.8 mg, 0.416 mmol) and NaOH (3.0 M, aq; 2.0 mL, 6.00 mmol) in dioxane (5.0 mL) was heated at 100° C. for 40 min. The reaction was cooled to RT and partitioned between DCM (50 mL) and H2O (30 mL). The organic layer was separated, and the aqueous layer was extracted with DCM (30 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0-100% (10% MeOH-EtOAc)/Hex) furnished 2-cyclopropyl-5-(3-(6-cyclopropylpyrazin-2-yl)-1H-indol-5-yl)-1,3,4-oxadiazole (71.0 mg, 0.207 mmol, 50%) as a yellow solid: MS (ESI, pos. ion) m/z: 344.2 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.03 (1H, br. s.), 9.06 (1H, d, J=1.4 Hz), 8.93 (1H, s), 8.41 (1H, s), 8.38 (1H, s), 7.82 (1H, dd, J=8.5, 1.7 Hz), 7.61 (1H, d, J=8.6 Hz), 2.29-2.38 (1H, m), 2.20-2.29 (1H, m), 1.13-1.25 (8H, m).

Fuente