Potassium Phosphate, Tribasic → US8598210, Table XV, 1

Temperature

85 °C

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.

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

ORD record

ord-1f67ec6d721e4d97b50f9259074064ef

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07811595B2