Potassium Phosphate, Tribasic → 1-(4-hydroxy-3-methoxyphenyl)-4-(4-(trifluoromethoxy)phenyl)pyridin-2(1H)-one

温度

90 °C

A mixture of 4-chloro-1-(3-methoxy-4-((2-(trimethylsilyl)ethoxy)methoxy)phenyl)-pyridin-2(1H)-one Part A (118 mg, 0.31 mmol), 4-(trifluoromethoxy)phenylboronic acid (95 mg, 0.463 mmol), Potassium phosphate tribasic (197 mg, 0.93 mmol), and PalladiumTetrakis (18 mg, 0.02 mmol) in DMF (1.5 mL) was stirred under nitrogen at 90° C. overnight. The mixture was diluted with DCM, filtered, and concentrated. The crude was dissolved in 10:90 MeOH/CH2Cl2 (5 mL) and 4N HCl in dioxane (1 mL) was added. The mixture was stirred for 30 min at RT. Concentrated and the residue was purified using ISCO flash chromatography (silica gel/hexanes/ethyl acetate/methanol 100:0 to 0:90:10 gradient) to afford the desired product 1-(4-hydroxy-3-methoxyphenyl)-4-(4-(trifluoromethoxy)phenyl)pyridin-2(1H)-one 14B (99 mg, 0.26 mmol, 85% yield) as a yellow solid. LC/MS 362 (M+H)+, tR 0.89 min (method 5).

1. filtrationfiltered
2. concentrationconcentrated
3. dissolutionThe crude was dissolved in 10:90 MeOH/CH2Cl2 (5 mL) and 4N HCl in dioxane (1 mL)
4. additionwas added
5. stirringThe mixture was stirred for 30 min at RT
6. concentrationConcentrated
7. customthe residue was purified

ORDレコード

ord-07e6776d0bf349d3983fb4deb62276c2

出典データセット

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08563583B2