反応 #2275698

反応方程式

[(3-hydroxy-5-trifluoromethane-sulfonyloxy-pyridine-2-carbonyl)-amino]-acetic acid methyl ester

3-chlorophenylboronic acid

K3PO4

→

desired compound

収率 53.0%

{[5-(3-chloro-phenyl)-3-hydroxy-pyridine-2-carbonyl]-amino}-acetic acid methyl ester

収率 53.0%

溶媒

1,4-dioxane

反応条件

後処理

1. 1
   温度After this time, the mixture is cooled to room temperature
2. 2
   濃縮concentrated under reduced pressure
3. 3
   workup.ADDITIONThe residue is then treated with 1M HCl (1 mL)
4. 4
   workup.ADDITIONdiluted with EtOAc
5. 5
   その他The organic layer is separated
6. 6
   洗浄washed with H2O, saturated aqueous NaCl
7. 7
   濃縮concentrated under reduced pressure
8. 8
   その他The crude material is purified over silica (EtOAc:heptane 3:7)
9. 9
   その他The resulting solid can be crystallized from EtOAc/heptane

実験手順

To a degassed solution of [(3-hydroxy-5-trifluoromethane-sulfonyloxy-pyridine-2-carbonyl)-amino]-acetic acid methyl ester, 5, (0.30 g, 0.84 mmol) in 1,4-dioxane (10 mL) at room temperature under N2 is added 3-chlorophenylboronic acid (0.196 g, 1.26 mmol), Pd(dppf)Cl2 (0.068 g, 0.0084 mmol) and K3PO4 (0.195 g, 0.92 mmol). The resulting suspension is heated in a sealed tube at 85° C. for 16 hours. After this time, the mixture is cooled to room temperature and concentrated under reduced pressure. The residue is then treated with 1M HCl (1 mL) and diluted with EtOAc. The organic layer is separated, washed with H2O, saturated aqueous NaCl and concentrated under reduced pressure. The crude material is purified over silica (EtOAc:heptane 3:7). The resulting solid can be crystallized from EtOAc/heptane to afford 0.143 g (53% yield) of the desired compound as a colorless solid. 1H NMR (400 MHz, CDCl3) δ ppm 11.77 (1H, s), 8.36 (1H, t, J=5.7 Hz), 8.24 (1H, d, J=1.8 Hz), 7.50-7.53 (1H, m), 7.39-7.42 (2H, m), 7.34-7.37 (2H, m), 4.20 (2H, d, J=5.9 Hz), 3.76 (3H, s). HPLC-MS: m/z.

出典