Ammonium Chloride → (5-{4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-phenyl}-pyridin-3-yl)-acetic Acid Methyl Ester

Temperature

100 °C

(5-Bromo-pyridin-3-yl)acetic acid methyl ester (Example 24-(2); 181 mg, 0.789 mmol), palladium acetate (12 mg, 0.053 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (22 mg, 0.053 mmol), potassium phosphate (335 mg, 1.578 mmol) and water (0.6 mL) were added to a solution of 4-{1-ethyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenol (Example 143-(3); 200 mg, 0.526 mmol) in toluene (6 mL). After replacement with nitrogen, the mixture was stirred at 100° C. for two hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, followed by extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 50:50) to give the target compound as a colorless oil (130.0 mg, 61%).

1. extractionfollowed by extraction with dichloromethane
2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
3. filtrationfiltered
4. concentrationconcentrated under reduced pressure
5. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 50:50)

ORD record

ord-d53b9810aa464572987b929700ec2480

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07935688B2