반응 #2275698

반응 방정식

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

3-chlorophenylboronic acid

K3PO4

→

desired compound

수율 53.0%

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

수율 53.0%

용매

1,4-dioxane

반응 조건

후처리

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

실험 절차

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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