반응 #92398

반응 방정식

N-(3-bromo-5-nitrophenyl)acetamide

pyrazole

cesium carbonate

→

N-(3-nitro-5-(1H-pyrazol-1-yl)phenyl)acetamide

수율 86.0%

용매

DMF

반응 조건

후처리

1. 1
   기타The mixture was quenched
2. 2
   추출extracted as in Example 1(d)
3. 3
   workup.DISTILLATIONThe solvent was distilled off
4. 4
   기타the residue was purified by column chromatography over silica gel (30% ethyl acetate in hexane)
5. 5
   기타to afford the compound in 86% yield (8.2 g)
6. 6
   기타247.1 [M+H]+ (rt: 0.6 min)

실험 절차

To a solution of N-(3-bromo-5-nitrophenyl)acetamide of Example 1(c) (10 g, 38.6 mmol) in DMF (100 ml) were added pyrazole (5.26 g, 77.2 mmol, 2.0 eq.), copper(I) oxide (1.104 g, 7.72 mmol, 0.2 eq.) and cesium carbonate (25.15 g, 77.2 mmol, 2.0 eq.) and the mixture was heated at 120° C. for 16 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off and the residue was purified by column chromatography over silica gel (30% ethyl acetate in hexane) to afford the compound in 86% yield (8.2 g). 1H NMR (300 MHz, DMSO-d6): δ 10.62 (s, 1H), 8.7 (d, 1H), 8.5-8.48 (m, 2H), 8.32 (t, 1H), 7.84 (d, 1H), 6.62 (t, 1H), 2.08 (s, 3H); LC-MS (ESI): Calculated mass: 246.22; Observed mass: 247.1 [M+H]+ (rt: 0.6 min).

출처