반응 #721372

반응 방정식

2-(3-(6-cyclopropylpyrazin-2-yl)-1H-indole-5-carbonyl)-N-phenylhydrazinecarboxamide

phosphorus oxychloride

→

5-(3-(6-cyclopropylpyrazin-2-yl)-1H-indol-5-yl)-N-phenyl-1,3,4-oxadiazol-2-amine

수율 32.0%

반응 조건

후처리

1. 1
   기타excess POCl3 was removed in vacuo
2. 2
   기타The residue was partitioned between EtOAc (80 mL) and saturated aq NaHCO3 (50 mL)
3. 3
   기타The organic layer was separated
4. 4
   세척washed with brine (30 mL)
5. 5
   건조dried over sodium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated in vacuo
8. 8
   기타Chromatographic purification of the residue (silica gel, 10-100% EtOAc/Hex)

실험 절차

A brown solution of 2-(3-(6-cyclopropylpyrazin-2-yl)-1H-indole-5-carbonyl)-N-phenylhydrazinecarboxamide (118.5 mg, 0.287 mmol) and phosphorus oxychloride (3.5 mL, 37.56 mmol) was stirred at 100° C. for 13 h. The reaction was cooled to RT, and excess POCl3 was removed in vacuo. The residue was partitioned between EtOAc (80 mL) and saturated aq NaHCO3 (50 mL). The organic layer was separated, washed with brine (30 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 10-100% EtOAc/Hex) furnished 5-(3-(6-cyclopropylpyrazin-2-yl)-1H-indol-5-yl)-N-phenyl-1,3,4-oxadiazol-2-amine (36.0 mg, 0.091 mmol, 32%) as a tan solid: MS (ESI, pos. ion) m/z: 395.1 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.01 (1H, br. s.), 10.53 (1H, s), 9.02 (1H, s), 8.91 (1H, s), 8.37 (1H, d, J=2.7 Hz), 8.36 (1H, s), 7.69-7.74 (1H, m), 7.63 (3H, dd, J=8.5, 1.7 Hz), 7.37 (2H, t, J=7.9 Hz), 7.02 (1H, t, J=7.3 Hz), 2.20-2.30 (1H, m), 1.16-1.21 (2H, m), 1.09-1.15 (2H, m).

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