تفاعل #90332

معادلة التفاعل

water

acetonitrile

[1,1′-biphenyl]-2-amine

cesium carbonate

2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acetyl azide

acetonitrile

→

title compound

المردود 28.0%

1-([1,1′-biphenyl]-2-yl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzyl)urea

المردود 28.0%

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted with ethyl acetate (3×25 mL)
2. 2
   تجفيفThe combined organic layers were dried over magnesium sulfate
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated
5. 5
   أخرىThe resulting residue was purified by flash chromatography

الإجراء التجريبي

A solution of 2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acetyl azide (0.100 g, 0.258 mmol) in acetonitrile (1.25 mL) was heated to 80° C. for 2.5 hours. The resulting solution was cooled to room temperature and [1,1′-biphenyl]-2-amine (0.0479 g, 0.283 mmol) and cesium carbonate (0.0920 g, 0.283 mmol) were added as solids. An additional amount of acetonitrile (1.0 mL) was added and the reaction was allowed to stir for 18 hours at room temperature. The reaction mixture was poured into water (20 mL) and extracted with ethyl acetate (3×25 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated. The resulting residue was purified by flash chromatography using 0-80% ethyl acetate/B, where B=1:1 dichloromethane/hexanes to afford the title compound as a white solid (0.039 g, 28%): 1H NMR (400 MHz, DMSO-d6) δ 9.40 (s, 1H), 8.12-8.04 (m, 4H), 7.90 (dd, J=8.2, 1.2 Hz, 1H), 7.63 (dq, J=9.0, 0.9 Hz, 2H), 7.55-7.46 (m, 3H), 7.45-7.36 (m, 5H), 7.33-7.26 (m, 1H), 7.18 (dd, J=7.6, 1.7 Hz, 1H), 7.14-7.06 (m, 2H), 4.32 (d, J=5.8 Hz, 2H); 19F NMR (376 MHz, DMSO-d6) δ −56.96; ESIMS m/z 530 ([M+H]+).

المصدر