تفاعل #1000724

معادلة التفاعل

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

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

Cs2CO3

CH3CN

→

title compound

المردود 81.0%

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

المردود 81.0%

المذيبات

EtOAc

ظروف التفاعل

المعالجة

1. 1
   غسيلwashed with water (15 mL), and brine (15 mL)
2. 2
   تجفيفThe organic portion was dried (MgSO4)
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated
5. 5
   workup.ADDITIONThe concentrated material was treated with 10% Et2O in hexanes (10 mL)
6. 6
   workup.STIRRINGstirred for 2 h
7. 7
   ترشيحThe resulting solid was filtered
8. 8
   غسيلrinsed with hexanes
9. 9
   أخرىdried

الإجراء التجريبي

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).

المصدر