반응 #40532

반응 방정식

2-amino-3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester

N-(methyl-2-pyridinyl)-6-methyl-4-trifluoromethylsulfonyloxy-2-pyridone

sodium carbonate

→

title compound

수율 175.4%

2-Amino-5-(5-methyl-3-oxo-4-pyridin-2-ylmethyl-cyclohexa-1,5-dienyl)-3-nitro-benzoic acid methyl ester

수율 175.4%

용매

ethylene glycol dimethylether

반응 조건

후처리

1. 1
   온도The resulting mixture was heated
2. 2
   온도at reflux for 3 hours
3. 3
   온도After cooling
4. 4
   농축concentration in vacuo the resulting dark solid
5. 5
   기타was purified (SiO2, 50% ethyl acetate/methylene chloride to 3% methanol in 50% ethyl acetate/methylene chloride)

실험 절차

To a solution of 2-amino-3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (0.163 g, 0.51 mmol) in ethylene glycol dimethylether (5 mL) was added N-(methyl-2-pyridinyl)-6-methyl-4-trifluoromethylsulfonyloxy-2-pyridone (0.136 g, 0.41 mmol), bis(triphenylphoshine)palladium (II) dichloride (0.029 g, 0.04 mmol), and sodium carbonate (0.62 mL, 1.24 mmol of 2M). The resulting mixture was heated at reflux for 3 hours. After cooling and concentration in vacuo the resulting dark solid was purified (SiO2, 50% ethyl acetate/methylene chloride to 3% methanol in 50% ethyl acetate/methylene chloride) to provide the title compound as an orange solid (0.176 g, 89%). 1H NMR (500 MHz, CDCl3) δ 2.41 (s, 3H), 3.39 (s, 3H), 5.5 (s, 2H), 6.28 (s, 1H), 6.68 (s, 1H), 7.3-7.1 (m, 2H), 7.62 (t, 1H), 8.49 (s, 1H), 8.61 (s, 1H).

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