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[ CAS No. 4373-60-8 ]

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2D
Chemical Structure| 4373-60-8
Chemical Structure| 4373-60-8
Structure of 4373-60-8 *Storage: {[proInfo.prStorage]}

Quality Control of [ 4373-60-8 ]

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Related Doc. of [ 4373-60-8 ]

SDS

Product Details of [ 4373-60-8 ]

CAS No. :4373-60-8MDL No. :MFCD09749846
Formula :C11H8BrNBoiling Point :311.9°C at 760 mmHg
Linear Structure Formula :NC5H4C6H4BrInChI Key :WLPFTJXVEBANAM-UHFFFAOYSA-N
M.W :234.09Pubchem ID :11115506
Synonyms :

Computed Properties of [ 4373-60-8 ]

TPSA : 12.9 H-Bond Acceptor Count : 1
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.00 Rotatable Bond Count : 1

Safety of [ 4373-60-8 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4373-60-8 ]

  • Downstream synthetic route of [ 4373-60-8 ]

[ 4373-60-8 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 4373-60-8 ]
  • 2-(2-[2H]-3-bromophenyl)pyridine [ No CAS ]
  • 2
  • [ 109-04-6 ]
  • [ 89598-96-9 ]
  • [ 4373-60-8 ]
YieldReaction ConditionsOperation in experiment
89% With nitrogen; In 1,2-dimethoxyethane; ethanol; hexane; water; ethyl acetate; 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 <strong>[4373-60-8]2-(3-bromophenyl)pyridine</strong> 1 as a colorless liquid 8.33 g in 89% yield. 1H NMR (CDCl3, Me4Si, 400 MHz): delta 7.25-7.28 (m, 1H), 7.34 (td, J=8.0, 1.2 Hz, 1H), 7.53-7.56 (m, 1H), 7.71 (dd, J=8.0, 0.8 Hz, 1H), 7.75-7.80 (m, 1H), 7.90-7.93 (m, 1H), 8.18-8.19 (m, 1H), 8.70-8.81 (m, 1H). 1H NMR (DMSO-d6, 400 MHz): delta 7.39-7.42 (m, 1H), 7.47 (t, J=8.0 Hz, 1H), 7.65 (dt, J=8.4, 0.8 Hz, 1H), 7.91 (tt, J=7.2, 0.8 Hz, 1H), 8.02-8.04 (m, 1H), 8.09-8.12 (m, 1H), 8.29-8.30 (m, 1H), 8.68-8.70 (m, 1H).
88% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; ethanol; water; at 80℃; for 24h; 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.
76% With palladium diacetate; potassium carbonate; triphenylphosphine; In 1,2-dimethoxyethane; water; for 8h;Inert atmosphere; Reflux; 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).
65% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 12h;Reflux; 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)
33.7% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 18.5h;Inert atmosphere; Reflux; Synthesis of <strong>[4373-60-8]2-(3-bromophenyl)pyridine</strong> 2-Bromopyridine (12.05 mLl, 127 mmol), 3-bromophenyl boronic acid (25.4 g, 127 mmol) and potassium carbonate (52.5 g, 380 mmol) were added to 9:1 mixture of toluene and water (600 mL). The reaction mixture was degassed with nitrogen gas for 15 minutes and Pd(PPh3)4 (1.463 g, 1.266 mmol) was added. The reaction mixture was degassed for another 30 minutes before heating to reflux under nitrogen gas for 18 hours. The crude reaction mixture was cooled to room temperature, filtered through a Celite pad and the filtrate was partitioned between brine and ethyl acetate. The organic layers were combined, dried over MgSO4 and the organic solvent was removed under reduced pressure. The crude product was purified by column chromatography over silica gel using 1-4% ethyl acetate/hexanes. 2-(3-bromophenyl) pyridine (10 g, 33.7%) was isolated as colorless oil.

  • 3
  • [ 101-82-6 ]
  • [ 4373-60-8 ]
  • 2-(phenyl-(3-(pyridin-2-yl)phenyl)methyl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With Bis(1,5-cyclooctadiene)nickel(0); lithium hexamethyldisilazane; nixantphos; at 60℃;Inert atmosphere; 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 <strong>[4373-60-8]2-(3-bromophenyl)pyridine</strong> (49.8 g, 213 mmol) in CPME (277 mL) was added to form a reaction mixture. The reaction mixture was heated to 60 C. for 2 hours, then the reaction mixture was cooled to room temperature and stirred for 12 hours. The reaction mixture was quenched with saturated aqueous ammonium chloride (500 mL) and solids were filtered through a pad of silica gel. After phase separation, the aqueous layer was extracted twice with ethyl acetate (500 mL each). The combined organic layers were washed with brine (500 mL), dried over Na2SO4, filtered and concentrated. The residue was stirred for 16 hours in hexanes to yield yellow solids, which were filtered and dried. The solids were dissolved in dichloromethane (DCM), adsorbed to silica gel, and purified by normal phase column chromatography (330 g HPLC, 10 to 60% EtOAc in Hexanes), which afforded 2-(phenyl(3-(pyridin-2-yl)phenyl)methyl)pyridine (40.1 g, 70% yield) as a yellow solid.
  • 4
  • [ 101-82-6 ]
  • [ 4373-60-8 ]
  • 2-(1-phenyl-1-(3-(pyridin-2-yl)phenyl)ethyl)pyridine [ No CAS ]
  • 5
  • [ 98061-22-4 ]
  • [ 4373-60-8 ]
  • C22H14N2OPt [ No CAS ]
  • 6
  • [ 98061-22-4 ]
  • [ 4373-60-8 ]
  • 2-(3-(3-(pyridin-2-yl)phenoxy)phenyl)pyridine [ No CAS ]
  • 7
  • [ 108-88-3 ]
  • [ 4373-60-8 ]
  • (4-bromo-2-(pyridin-2-yl)phenyl)(phenyl)methanone [ No CAS ]
  • 8
  • [ 4373-60-8 ]
  • 8-(4-(2-(4-(3-(pyridin-2-yl)phenyl)piperidin-1-yl)ethyl)-1H-pyrazol-1-yl)pyrido[3,4-d]pyrimidin-4(3H)-one [ No CAS ]
  • 9
  • [ 4373-60-8 ]
  • 8-(4-(2-(4-(3-(pyridin-2-yl)phenyl)piperidin-1-yl)ethyl)-1H-pyrazol-1-yl)-3-((2-(trimethylsilyl)ethoxy)methyl)pyrido[3,4-d]pyrimidin-4(3H)-one [ No CAS ]
  • 10
  • [ 4373-60-8 ]
  • 2-(3-(piperidin-4-yl)phenyl)pyridine [ No CAS ]
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