反应 #40530

反应方程式

NaHCO3

pyridine-3-boronic acid 1,3-propanediol cyclic ester

(2-amino-5-bromo-3-nitro-phenyl)-cyclohexyl-methanone

→

title compound

收率 89.0%

(2-Amino-3-nitro-5-pyridin-3-yl-phenyl)-cyclohexyl-methanone

收率 89.0%

溶剂

EtOAc

DME

反应条件

后处理

1. 1
   洗涤washed with water (50 mL), brine (50 mL)
2. 2
   干燥dried (MgSO4)
3. 3
   过滤filtered
4. 4
   浓缩the filtrate concentrated in vacuo
5. 5
   其他The resulting residue was purified by flash chromatography (SiO2, hexanes to 3:1 hexanes:EtOAc)

实验过程

To a solution of (2-amino-5-bromo-3-nitro-phenyl)-cyclohexyl-methanone (600 mg, 1.83 mmol) in DME (25 mL) was added, successively, pyridine-3-boronic acid 1,3-propanediol cyclic ester (388 mg, 2.38 mmol), (tetrakistriphenylphosphine) palladium(0) (212 mg, 0.18 mmol), and 1N NaHCO3 (3.7 mL, 3.7 mmol). The resulting mixture was stared at 90° C. for 90 minutes then cooled to room temperature. The reaction mixture was diluted with EtOAc (100 mL), washed with water (50 mL), brine (50 mL), dried (MgSO4), filtered and the filtrate concentrated in vacuo. The resulting residue was purified by flash chromatography (SiO2, hexanes to 3:1 hexanes:EtOAc) to afford 527 mg (89%) of the title compound as a pale orange solid: 1H NMR (CDCl3, 500 MHz) δ 8.92 (d, 1H), 8.69 (d, 1H), 8.66 (d, 1H), 8.31 (d, 1H), 8.20 (d, 1H), 7.71 (dd, 1H), 3.36 (m, 1H), 1.88 (m, 3H), 1.77 (m, 1H), 1.40-1.61 (m, 3H), 1.24-1.32 (m, 2H), 0.89 (m, 1H).

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