Potassium Carbonate → methyl [2-fluoro-4-(2-oxo-1(2H)-pyridinyl)phenyl]acetate

온도

125 °C

Part G. To methyl (2-fluoro-4-iodophenyl)acetate (1.0 g, 3.4 mmol) in dimethylsulfoxide (68 mL) was added potassium carbonate (1.9 g, 14 mmol) and 2-hydroxypyridine (650 mg, 6.8 mmol). The resulting mixture was degassed (alternate vacuum/nitrogen three times), and copper(I) iodide (650 mg, 3.4 mmol) was added in one portion. The light green mixture was again degassed (vac/N2) and warmed to 125° C. After 14 h, the brown-black mixture was cooled and poured into saturated aqueous ammonium hydroxide (50 mL) and ethyl acetate (100 mL). The layers were separated, and the organic layers were washed with water (2×50 mL) and saturated aqueous sodium chloride. The organic layers were concentrated, and the resulting residue was purified by radial chromatography (20–100% ethyl acetate in hexanes) to afford methyl [2-fluoro-4-(2-oxo-1(2H)-pyridinyl)phenyl]acetate (340 mg, 39%) as a green-brown solid. LC/MS (ESI+): 262.2 (M+H)+. 1H NMR (CDCl3) δ 7.22–7.36 (m, 3H), 7.08 (t, 2H), 6.54 (d, 1H), 6.18 (t, 1H), 3.63 (s, 5H).

1. additionwas added in one portion
2. customThe light green mixture was again degassed (vac/N2)
3. temperaturethe brown-black mixture was cooled
4. additionpoured into saturated aqueous ammonium hydroxide (50 mL) and ethyl acetate (100 mL)
5. customThe layers were separated
6. washthe organic layers were washed with water (2×50 mL) and saturated aqueous sodium chloride
7. concentrationThe organic layers were concentrated
8. customthe resulting residue was purified by radial chromatography (20–100% ethyl acetate in hexanes)

ORD 기록

ord-ef0955e650dc492c9bc5727a4bbfe181

출처 데이터셋

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06995172B2