2-(3-Bromophenyl)pyridine

light yellow liquid

To a three-necked flask equipped with a magnetic stir bar and a condenser, added 3-bromophenylboronic acid (8033 mg, 40 mmol) and K2CO3 (12.16 g, 88 mmol). The flask was sealed and then evacuated and backfilled with nitrogen. Repeated the evacuation and backfill procedure four additional times. After that solvents DME (100 mL), EtOH (32 mL) and H2O (44 mL) were added independently by syringe. The mixture was bubbled with nitrogen through a needle for 30 minutes. Then 2-bromopyridine (3.89 mL, 40 mmol) and Pd(PPh3)4 (924 mg, 0.8 mmol) were added under the atmosphere of nitrogen. The mixture was heated to reflux (about 95-105 C.) in an oil bath. The reaction was monitored by TLC and about 24 hours later the reaction was completed. Then cooled down to ambient temperature and water was added until the salt dissolved completely. Then the organic layer was separated and the aqueous layer was extracted with ethyl acetate for twice. The combined organic layer was dried over sodium sulfate. Then filtered and washed with ethyl acetate. The filtrate was concentrated under reduced pressure using a rotary evaporator and the residue was purified through column chromatography on silica gel using hexane and ethyl acetate (20:1) as eluent to afford the desired product To an oven-dried flask were added (3-bromophenyl)boronic acid (1.1 eq), 2-bromopyridine (1 eq), Pd(PPh3)4 (0.1 eq), EtOH/H2O (3:3:1 ratio, 0.2 M for EtOH) and aqueous K2CO3 (2 M, 10 eq). The mixture was heated in an 80 C. oil bath for 24 hours. The mixture was cooled to room temperature. The solvent was then removed under reduced pressure. The product was isolated by column chromatography (Hexane:EtOAc=15:1 to 8:1) in 88% yield.2-bromopyridine (75.0 g, 475 mmol), 3-bromophenylboronic acid (104.8 g, 520 mmol), palladium acetate (2.6 g, 2.5 mol %), triphenylphosphine (5.37 g, 5 mol %) and potassium carbonate (196.0 g, 1425 mmol) was placed in a 2 L 3-neck round bottom flask. 500 mL of dimethoxyethane and 500 mL of H2O was added to the flask. Nitrogen was bubbled through the solution for 30 minutes and then the solution was refluxed for 8 h in an atmosphere of nitrogen. The reaction was then allowed to cool to room temperature and the organic phase was separated from the aqueous phase. The aqueous phase was washed with ethylacetate and the organic fractions were combined and dried over magnesium sulfate and the solvent removed under vacuum. The product was chromatographed using silica gel with ethylacetate and hexanes as the eluent. The solvent was removed to give 84.0 g of a clear oil (76% yield).To a 500 ml round bottom flask was added 20.0 g (127 mmol) of 3-bromophenylboronic acid, 25.4 g (127 mmol) of 2-bromopyridine, 2.93 g (2.53 mmol) of tetrakistriphenylphosphine palladium, 40 ml of a 2M sodium carbonate aqueous solution, 40 ml of ethanol and 200 ml of toluene were added and refluxed for 12 hours. The temperature was lowered to room temperature and the reaction was terminated and filtered. The organic layer was extracted with diethyl ether and water, concentrated under reduced pressure, Column purification was carried out using ethyl acetate and n-hexane as eluent.(19.3 g, 65% yield)Synthesis of Step 1-Synthesis of 2-(phenyl(3-(pyridin-2-yl)phenyl)methyl)pyridine A 1-liter 3-neck RBF equipped with a stir bar was charged with 4, 6-bis(diphenylphosphino)-10H-phenoxazine (NxantPhos) (4.89 g, 8.86 mmol) and bis(cyclooctadiene)nickel(0) (Ni(cod)2) (2.44 g, 8.86 mmol) under argon atmosphere. Cyclopentyl methyl ether (CPME) (1500 mL) was then added to form a dark orange slurry, which was degassed for 30 minutes. Then, lithium bis(trimethylsilyl)amide (LiHMDS) (1 M, 372 mL, 372 mmol) was added slowly followed by 2-benzyl pyridine (28.3 mL, 177 mmol). A previously degassed solution of

Molecular Weight:234.09
XLogP3:3.3
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:232.98401
Monoisotopic Mass:232.98401
Topological Polar Surface Area:12.9
Heavy Atom Count:13
Complexity:160
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes