반응 #721386

반응 방정식

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

수율 50.0%

용매

dioxane

반응 조건

후처리

1. 1
   기타partitioned between DCM (50 mL) and H2O (30 mL)
2. 2
   기타The organic layer was separated
3. 3
   추출the aqueous layer was extracted with DCM (30 mL)
4. 4
   건조The combined organic extracts were dried over sodium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo
7. 7
   기타Chromatographic purification of the residue (silica gel, 0-100% (10% MeOH-EtOAc)/Hex)

실험 절차

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).

출처