Reaktion #2275698

Reaktionsgleichung

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

3-chlorophenylboronic acid

K3PO4

→

desired compound

Ausbeute 53.0%

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

Ausbeute 53.0%

Lösungsmittel

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

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