반응 #1000724

반응 방정식

2-propyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

5-[3,5-bis(trifluoromethyl)phenyl]-3-(chloromethyl)-1,2,4-oxadiazole

Cs2CO3

CH3CN

→

title compound

수율 81.0%

1-({5-[3,5-Bis(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-2-propyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

수율 81.0%

용매

EtOAc

반응 조건

후처리

1. 1
   세척washed with water (15 mL), and brine (15 mL)
2. 2
   건조The organic portion was dried (MgSO4)
3. 3
   여과filtered
4. 4
   농축concentrated
5. 5
   workup.ADDITIONThe concentrated material was treated with 10% Et2O in hexanes (10 mL)
6. 6
   workup.STIRRINGstirred for 2 h
7. 7
   여과The resulting solid was filtered
8. 8
   세척rinsed with hexanes
9. 9
   기타dried

실험 절차

A mixture of 2-propyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile (0.040 g, 0.16 mmol), 5-[3,5-bis(trifluoromethyl)phenyl]-3-(chloromethyl)-1,2,4-oxadiazole (0.058 g, 0.17 mmol), Cs2CO3 (0.057 g, 0.17 mmol) and CH3CN (4 mL) was stirred at 75° C. for 1.5 h. The mixture was diluted with EtOAc (25 mL), washed with water (15 mL), and brine (15 mL). The organic portion was dried (MgSO4), filtered, and concentrated. The concentrated material was treated with 10% Et2O in hexanes (10 mL) and stirred for 2 h. The resulting solid was filtered, rinsed with hexanes, and dried to afford the title compound (0.070 g, 81%) as a light tan solid: 1H NMR (400 MHz, DMSO-d6) δ 8.53 (s, 2H), 8.50 (s, 1H), 8.03 (d, J=8.6 Hz, 1H), 7.75 (d, J=8.6 Hz, 1H), 6.59 (s, 1H), 5.90 (s, 2H), 2.90 (t, J=7.5 Hz, 2H), 1.79-1.70 (m, 2H), 0.98 (t, J=7.4 Hz, 3H); MS m/z 547 (M+H).

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