Reaktion #634145

Reaktionsgleichung

(4-Chloro-2-fluoro-phenyl)acetic acid methyl ester

(4-chloro-2-fluoro-phenyl)-acetic Acid Methyl Ester

2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl

potassium phosphate

1-[(E)-2-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-vinyl]-cyclopentanol

sodium bicarbonate

→

title compound

Ausbeute 30.0%

[4′-(1-ethyl-1-{4-[(E)-2-(1-hydroxy-cyclopentyl)-vinyl]-3-methyl-phenyl}-propyl)-3-fluoro-2′-methyl-biphenyl-4-yl]-acetic Acid Methyl Ester

Ausbeute 30.0%

Lösungsmittel

water

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe aqueous layer was extracted with dichloromethane
2. 2
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   SonstigeThe residue was purified by silica gel chromatography (17% ethyl acetate/hexane)

Vorschrift

(4-Chloro-2-fluoro-phenyl)acetic acid methyl ester (Example 40; 47 mg, 0.230 mmol), toluene (2.5 mL), palladium acetate (3.4 mg, 0.015 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (12.6 mg, 0.031 mmol), potassium phosphate (97 mg, 0.459 mmol) and water (0.250 mL) were added to 1-[(E)-2-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-vinyl]-cyclopentanol (Example 33-(3); 75 mg, 0.153 mmol), and the mixture was stirred in a nitrogen atmosphere at 100° C. for two hours. The reaction solution was poured into a saturated aqueous sodium bicarbonate solution, and then the aqueous layer was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (17% ethyl acetate/hexane) to give the title compound (24 mg, 30%).

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