[3-(PYRID-2-YLOXY)PHENYL]METHANOL synthesis

Yield:869901-22-4 71 %

Reaction Conditions:

with caesium carbonate in N,N-dimethyl-formamide at 100;

Steps:

2.1 Step 1

To a solution of 2-fLuoro-pyridine (25.8 g, 0.27 mol) in DMF (300 mL) was added 3-hydroxyphenyl-methanol (30.0 g, 0.24 mol) and cesium carbonate (117.3 g, 0.36 mol) at room temperature. The reaction mixture was stirred at 100 °C over a period of 5 h. Then the resulting mixture was ahowed to reach room temperature, diluted with water (250 mL), extracted with ethyl acetate (3X500 mL) and the organic layer was dried over sodium sulphate. The crude product obtained upon evaporation of volatiles was purified through silica gel (230- 400) column (30% ethyl acetate in petroleum ether) to give product 2 as a pale yellow oil 34.5 g (71 %). ¹H NMR (300 MHz, DMSO-d6) δ (ppm): 4.49-4.51 (m, 2H), 5.24-5.30 (m, 1H), 6.98-7.15 (m, 5H), 7.33-7.40 (m, 1H), 7.82-7.89 (m, 1H), 8.14- 8.16 (m, 1H).

References:

WO2022/221493,2022,A1 Location in patent:Paragraph 0229-0231