[ CAS No. 57311-18-9 ] {[proInfo.proName]}

Name: 57311-18-9|4-Chloro-2-phenylpyridine|96%
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Quality Control of [ 57311-18-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 57311-18-9 ]

Product Details of [ 57311-18-9 ]

CAS No. :	57311-18-9	MDL No. :	MFCD04114166
Formula :	C₁₁H₈ClN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BFRWDRFLYBYSFX-UHFFFAOYSA-N
M.W :	189.64	Pubchem ID :	2762846
Synonyms :

Calculated chemistry of [ 57311-18-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	54.68
TPSA :	12.89 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.0 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.29
Log Po/w (XLOGP3) :	3.46
Log Po/w (WLOGP) :	3.4
Log Po/w (MLOGP) :	2.68
Log Po/w (SILICOS-IT) :	3.67
Consensus Log Po/w :	3.1

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.81
Solubility :	0.0292 mg/ml ; 0.000154 mol/l
Class :	Soluble
Log S (Ali) :	-3.41
Solubility :	0.0734 mg/ml ; 0.000387 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.16
Solubility :	0.00131 mg/ml ; 0.00000692 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.65

Safety of [ 57311-18-9 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 57311-18-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 57311-18-9 ]

[ 57311-18-9 ] Synthesis Path-Downstream 1~50

1
4-Chloro-2-phenyl-2H-pyridine-1-carboxylic acid phenyl ester [ No CAS ]
[ 57311-18-9 ]

Yield	Reaction Conditions	Operation in experiment
	With o-tetrachloroquinone; acetic acid In toluene for 24h; Ambient temperature; Yield given;

Reference： [1]Comins, Daniel L.; Mantlo, Nathan B. [Journal of Organic Chemistry, 1985, vol. 50, # 22, p. 4410 - 4411]

2
[ 1131-33-5 ]
[ 57311-18-9 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate In chloroform

Reference： [1]Thomson, Christopher G.; Beer, Margaret S.; Curtis, Neil R.; Diggle, Helen J.; Handford, Emma; Kulagowski, Janusz J. [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 3, p. 677 - 680]

3
[ 57311-18-9 ]
[ 13242-44-9 ]
dimethyl-[2-(2-phenyl-pyridin-4-ylsulfanyl)-ethyl]-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In N,N-dimethyl-formamide

4
[ 1121-76-2 ]
[ 100-59-4 ]
[ 57311-18-9 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 1335 - 1337
[2]Chemical Communications,2010,vol. 46,p. 3384 - 3386
[3]Synthesis,2015,vol. 46

5
[ 872-50-4 ]
[ 57311-18-9 ]
[ 100-02-7 ]
[ 7087-68-5 ]
[ 417721-23-4 ]
[ 417724-78-8 ]

Yield	Reaction Conditions	Operation in experiment
	In water; ethyl acetate	P.124.1 4-(2-Phenylpyridin-4-yl)oxyaniline Production Example 124-1 4-(2-Phenylpyridin-4-yl)oxyaniline 4-Chloro-2-phenylpyridine 1.0 g (5.5 mM), paranitrophenol (1.68 g, 12 mM), Hunig's base (diisopropylethylamine, 5 ml) and 1-methylpyrrolidone (10 ml) were stirred at 160° C. for 20 hours. Water was added, extraction was performed with ethyl acetate, and the organic layer was washed 5 times with water. The solvent was distilled off under reduced pressure and the residue was purified by silica gel chromatography (hexane:ethylacetate=4:1) to obtain 490 mg of 4-(4-nitrophenoxy)-2-phenylpyridine as a light yellow solid. 1H-NMR(DMSO-d6) δ (ppm): 7.08-7.14 (1H, m), 7.40-7.53 (5H, m), 7.74 (1H, s), 8.07-8.13 (2H, m) 8.34 (2H, d, J=8.8 Hz), 8.68 (1H, dd, J=5.6 Hz, J=1.2 Hz).

Reference： [1]Current Patent Assignee: JPARIMOTO ITARU; EISAI CO LTD - US2004/53908, 2004, A1

6
[ 57311-18-9 ]
[ 156-57-0 ]
[ 1265869-41-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	Stage #1: 2-mercaptoethylamine hydrochloride With sodium hydride In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; Inert atmosphere; Cooling with ice; Stage #2: 4-chloro-2-phenyl-pyridine In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 3.16667h; Inert atmosphere;	3.4. General procedure (C) for reaction of 2-amino-ethanethiol·HCl with halogen-substituted N-heterocycles General procedure: 2-Aminoethanethiol hydrochloride (1.1-1.2 equiv) was suspended in dry HMPA (1-4 mL). NaH (dry, 95%) (2.4-2.6 equiv) was added portion-wise over 10-20 min while the reaction mixture was cooled in an ice-cold water bath under a nitrogen atmosphere. The mixture was stirred for 10 min at ambient temperature before portion-wise addition of the desired halogenated heterocycle (1.22-17.5 mmol, 1 equiv) over 10 min. The reaction mixture was stirred at ambient temperature for 2 h-2 days. Water was added slowly to quench the reaction then the aqueous layer was extracted with CH2Cl2, and the combined organic extract dried (MgSO4), filtered and solvent removed in vacuo to give the crude product. TLC on silica using CH2Cl2/MeOH/NH3 in MeOH, 9:0.8:0.2 showed the products with Rf values in the range 0.15-0.20.

Reference： [1]Location in patent: experimental part Mountford, Simon J.; Campi, Eva M.; Robinson, Andrea J.; Hearn, Milton T.W. [Tetrahedron, 2011, vol. 67, # 2, p. 471 - 485]

7
[ 26452-80-2 ]
[ 98-80-6 ]
[ 57311-18-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium carbonate In 1,2-dimethoxyethane; water for 20h; Reflux;	1 Step 1 Synthesis of 4-chloro-2-phenylpyridine A 1 L round bottom flask was charged with 2,4-dichloropyridine (30 g, 203 mmol), phenylboronic acid (24.7 g, 203 mmol), potassium carbonate (84 g, 608 mmol), Pd(PPh3)4 (2.3 g, 2.0 mmol), dimethoxyethane (500 mL) and water (150 mL). The reaction mixture was degassed and heated to reflux for 20 h. After cooling and separation of the layers, the aqueous layer was extracted with EtOAc (2*100 mL). After removal of the solvent, the crude product was subjected to column chromatography (SiO2, 5% EtOAc in hexane to 10% EtOAc in hexane) to get 34 g (88% yield) of pure product.
88%	With SiO₂ In 1,2-dimethoxyethane; hexane; water; ethyl acetate	Synthesis of 4-chloro-2-phenylpyridine Synthesis of 4-chloro-2-phenylpyridine A 1 L round bottom flask was charged with 2,4-dichloropyridine (30 g, 203 mmol), phenylboronic acid (24.7 g, 203 mmol), potassium carbonate (84 g, 608 mmol), Pd(PPh3)4 (2.3 g, 2.0 mmol), dimethoxyethane (500 mL) and water (150 mL). The mixture was degassed and heated to reflux for 20 h. After cooling, the aqueous layer was extracted with EtOAc; the organic portion was combined and subjected to column chromatography (SiO2, 5% EtOAc in hexane to 10% EtOAc in hexane) to give 34 g (88%) of 4-chloro-2-phenylpyridine. The product was confirmed by GC/MS and NMR.
88%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,2-dimethoxyethane; water for 20h; Reflux;	synthesis of 4-chloro-2-phenyl pyridine 1 L round bottom flask in feed-in 2,4-dichloro-pyridine (30 g, 203 mmol), phenyl Acid (24.7 g, 203 mmol), potassium carbonate (84 g, 608 mmol), Pd (PPh3)4(2.3 g, 2.0 mmol), dimethoxy ethane (500 ml) and water (150 ml). The mixture is heated to reflux and degasification 20 h. After cooling, EtOAc extraction the aqueous layer for; and the combined organic portion of the organic part of the experience column chromatography (SiO2, 5% EtOAc in hexane to 10% EtOAc in hexane for), obtain 34 g (88%) 4-chloro-2-phenyl-pyridine. GC/MS and NMR confirmed the product.

80%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,2-dimethoxyethane; water for 2h; Inert atmosphere; Microwave irradiation; Reflux;	1.1 Step 1: Synthesis of 4-chloro-2-phenylpyridine first,12 g of 2,4-dichloropyridine, 9.9 g of phenylboronic acid, 34 g of potassium carbonate, 400 mL of DME, 240 mL of water was placed in a three-necked flask equipped with a reflux tube,The inside of the flask was purged with nitrogen. Further 0.94 g of tetrakis(triphenylphosphine)palladium(0) was added and irradiated with microwave (2.45 GHz, 400 W) for 2 hours.After the reaction, extraction with ethyl acetate was carried out. Thereafter, purification was carried out by silica gel column chromatography using dichloromethane as a developing solvent,12 g (yield 80%, yellow oil) of the target product was obtained.The synthesis scheme of Step 1 is shown in the following (a-1).
65%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 18h; Inert atmosphere;	2.2.1. Synthesis of 4-chloro-2-phenylpyridine Phenylboronic acid (3.0 g, 25 mmol), 2,4-dichloropyridine (3.7 g,25 mmol), Pd(PPh3)4 (0.87 g, 0.75 mmol) and K2CO3 (10.4 g, 75 mmol) were dissolved in 1,2-dimethoxyethane/H2O (70/30 mL). The mixture was stirred at 90 °C under a nitrogen atmosphere for 18 h. After being cooled to room temperature, the mixture was extracted with CH2Cl2 (3 × 50 mL). The organic phase was washed with brine, dried over anhydrous Na2SO4 and purified by column chromatography on silica gel with petroleum ether/CH2Cl2 (5:1) as the eluent, yielding a lightyellow oil (3.1 g, 16.9 mmol).Yield: 65%. 1H NMR (CDCl3, 400 MHz, δ [ppm]): δ 8.59 (d, J=5.3 Hz, 1H), 8.00-7.95 (m, 2H), 7.74 (d,J=1.8 Hz, 1H), 7.52-7.42 (m, 3H), 7.24-7.27 (m, 1H). HRMS (ESI, m/z): 190.0407 [M+H]+ (calc. 190.0418).
47.4 g	Stage #1: 2,4-dichloropyridine; phenylboronic acid With potassium carbonate In 1,2-dimethoxyethane; water for 0.75h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In 1,2-dimethoxyethane; water Reflux; Inert atmosphere;	3.A 2-phenyl-4-chloro-pyridine 2,4-Dichloropyridine (42.6 g, 0.2879 mol), phenylboronic acid (36.0 g, 0.2953 mol), 396 ml water, 840 ml monoglyme and potassium carbonate (102 g, 0..738 mol) were sparged with nitrogen for 45 minutes. Tetrakistriphenylphosphine Pd(0) (6.6 g, 5.7 mmol) was quickly added and the mixture was refluxed overnight. After cooling the mixture was concentrated and taken up in methylene chloride and washed with several water extractions. The methylene chloride solution was purified by silica flash chromatography using methylene chloride/hexanes as eluent. Products cuts were concentrated to 47.4 grams of yellow oil
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,2-dimethoxyethane; water for 16h; Inert atmosphere; Reflux;	23 Synthesis of 2-phenyl-4-chloropyridine Synthesis of 2-phenyl-4-chloropyridine 2,4-dichloropyridine (10 g, 67.57 mmol), phenylboronic acid (9.0 g, 74.32 mmol), and potassium carbonate (28 g, 202.70 mmol), 300 mL dimethoxyethane and 30 mL of water was placed in a 1 L round-bottom flask. Nitrogen was bubbled directly into the mixture for 30 min. Tetrakis(triphenylphosphine)palladium(0) (780 mg, 0.675 mmol) was added and nitrogen was bubbled into the reaction mixture for a another 15 min. The reaction mixture was then heated to reflux under nitrogen for 16 h. The reaction was then allowed to cool to room temperature and diluted with ethyl acetate and water. The organic and aqueous layers were separated and the aqueous layer was extracted with ethyl acetate. The organic layers were combined and washed with a saturated brine solution. The organic layer was then dried over magnesium sulfate, filtered, and the solvent was removed under vacuum to give an off-white solid as crude. The crude was purified by column chromatography using silica gel as the stationary phase and 2% ethyl acetate in hexanes as the mobile phase. 8.0 g of desired product was obtained after purification (54% yield). 11.5 g of desired product was obtained after purification (89.77% yield).

Reference： [1]Current Patent Assignee: UNIVERSAL DISPLAY CORP - US2012/299468, 2012, A1 Location in patent: Page/Page column 59
[2]Current Patent Assignee: UNIVERSAL DISPLAY CORP - US2013/26452, 2013, A1 Location in patent: Page/Page column
[3]Current Patent Assignee: UNIVERSAL DISPLAY CORP - TWI523860, 2016, B Location in patent: Page/Page column 93
[4]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - JP2018/52929, 2018, A Location in patent: Paragraph 0304; 0306; 0307
[5]Meng, Xianwen; Bai, Rubing; Wang, Xiaoxiang; Pan, FangFang; He, Lei [Dyes and Pigments, 2019, vol. 165, p. 458 - 466]
[6]Current Patent Assignee: LG CHEM CO.,LTD. - WO2013/142633, 2013, A1 Location in patent: Page/Page column 31; 32
[7]Current Patent Assignee: UNIVERSAL DISPLAY CORP - US2015/307535, 2015, A1 Location in patent: Paragraph 0239; 0240

8
[ 57311-18-9 ]
[ 153624-38-5 ]
[ 1414972-03-4 ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium phosphate In water; toluene for 21h; Reflux;	1 Step 1 Synthesis of 4-(4-isobutylphenyl)-2-phenylpyridine A 250 mL round-bottomed flask was charged with 4-chloro-2-phenylpyridine (5 g, 26.4 mmol), (4-isobutylphenyl)boronic acid (7.04 g, 39.5 mmol), Pd2(dba)3(0.483 g, 0.527 mmol), dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-3-yl)phosphine (S-Phos) (0.866 g, 2.109 mmol), K3PO4(16.79 g, 79 mmol), toluene (100 mL) and water (10 mL) to give a yellow suspension. The suspension was heated to reflux for 21 hrs. The reaction mixture was poured into water and extracted with EtOAc. The organic layers were combined and subjected to column chromatography (SiO2, 10% EtOAc in hexane) to yield 4-(4-isobutylphenyl)-2-phenylpyridine (6 g, 20.9 mmol, 79% yield).

Reference： [1]Current Patent Assignee: UNIVERSAL DISPLAY CORP - US2012/299468, 2012, A1 Location in patent: Page/Page column 60-61

9
[ 57311-18-9 ]
[ 1312471-21-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium phosphate / toluene; water / 0.33 h / Inert atmosphere 1.2: 18 h / Reflux 2.1: hydrogen / platinum on activated charcoal; palladium on activated charcoal / ethanol / 2 h / 4344.16 Torr / Inert atmosphere
	Multi-step reaction with 2 steps 1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / water; toluene / 18 h / Inert atmosphere; Reflux 2: palladium on activated charcoal; hydrogen / ethanol / 2 h / Inert atmosphere

Reference： [1]Current Patent Assignee: UNIVERSAL DISPLAY CORP - US2012/299468, 2012, A1
[2]Current Patent Assignee: UNIVERSAL DISPLAY CORP - TWI523860, 2016, B

10
[ 57311-18-9 ]
C₅₆H₅₆Cl₂Ir₂N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: potassium phosphate / toluene; water / 0.33 h / Inert atmosphere 1.2: 18 h / Reflux 2.1: hydrogen / platinum on activated charcoal; palladium on activated charcoal / ethanol / 2 h / 4344.16 Torr / Inert atmosphere 3.1: 2-ethoxy-ethanol; water / 18 h / 130 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / water; toluene / 18 h / Inert atmosphere; Reflux 2: palladium on activated charcoal; hydrogen / ethanol / 2 h / Inert atmosphere 3: 2-ethoxy-ethanol; water / 18 h / 130 °C / Inert atmosphere; Reflux

Reference： [1]Current Patent Assignee: UNIVERSAL DISPLAY CORP - US2012/299468, 2012, A1
[2]Current Patent Assignee: UNIVERSAL DISPLAY CORP - TWI523860, 2016, B

11
[ 57311-18-9 ]
C₂F₃O₂^(1-)*C₃₀H₃₆IrN₂O₂⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: potassium phosphate / toluene; water / 0.33 h / Inert atmosphere 1.2: 18 h / Reflux 2.1: hydrogen / platinum on activated charcoal; palladium on activated charcoal / ethanol / 2 h / 4344.16 Torr / Inert atmosphere 3.1: 2-ethoxy-ethanol; water / 18 h / 130 °C / Inert atmosphere 4.1: dichloromethane / 20 °C

Reference： [1]Current Patent Assignee: UNIVERSAL DISPLAY CORP - US2012/299468, 2012, A1

12
[ 57311-18-9 ]
C₄₅H₄₀IrN₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: potassium phosphate / toluene; water / 0.33 h / Inert atmosphere 1.2: 18 h / Reflux 2.1: hydrogen / platinum on activated charcoal; palladium on activated charcoal / ethanol / 2 h / 4344.16 Torr / Inert atmosphere 3.1: 2-ethoxy-ethanol; water / 18 h / 130 °C / Inert atmosphere 4.1: dichloromethane / 20 °C 5.1: ethanol; methanol / 20 h / Reflux; Inert atmosphere

Reference： [1]Current Patent Assignee: UNIVERSAL DISPLAY CORP - US2012/299468, 2012, A1

13
[ 57311-18-9 ]
C₄₃H₃₆IrN₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium phosphate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / 21 h / Reflux 2: ethanol; methanol / 20 h / Reflux; Inert atmosphere

Reference： [1]Current Patent Assignee: UNIVERSAL DISPLAY CORP - US2012/299468, 2012, A1

14
[ 57311-18-9 ]
[ 126726-62-3 ]
[ 1414972-01-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: 4-chloro-2-phenyl-pyridine With potassium phosphate In water; toluene for 0.333333h; Inert atmosphere; Stage #2: 2-isopropenyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane In water; toluene for 18h; Reflux;	2 Step 2 Synthesis of 2-phenyl-4-(prop-1-en-2yl)pyridine 4-Chloro-2-phenylpyridine (14.0 g, 73.8 mmol) and potassium phosphate (51.0 g, 221 mmol) were dissolved in 300 mL of toluene and 30 mL of water. The reaction was purged with nitrogen for 20 minutes and then 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (16.65 mL, 89 mmol), Pd2(dba)3 (1.35 g, 1.48 mmol) and S-Phos (2.42 g, 5.91 mmol) were added. The reaction was refluxed for 18 h. After cooling, 100 mL of water was added, the layers were separated, and the aqueous layer extracted twice with 100 mL of ethyl acetate. The organic layers were passed through a plug of silica gel, eluting with DCM. After evaporation of the solvent, the crude product was subjected to column chromatography (SiO2, 5% EtOAc in hexane to 10% EtOAc in hexane) to get 13.5 g of pure product (90% yield).
90%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ In water; toluene for 18h; Inert atmosphere; Reflux;	synthesis of 2-phenyl-4- (prop-1-en-2-yl) pyridine A mixture of 4-chloro-2-phenyl-pyridine (14 g, 73.8 mmol) and potassium (51.0 g, 221 mmol) was dissolved phosphate in 300 mL of toluene and 30 mL of water.The reaction was purged with nitrogen for 20 minutes, followed by addition of 4,4,5,5-tetramethyl-2- (prop-1-en-2-yl) 1,3,2-dioxaborolane (16.65 mL, mmol 89), of Pd2(DBA)3(1.35 G, 1.48 mmol) and S-Phos (2.42 g, 5.91 mmol).The reaction was refluxed for 18 h.After cooling, 100 mL of water, separated and the aqueous layer was extracted twice with 100 mL of ethyl acetate.The organic layer silicone plug, eluting with DCM.After evaporating the solvent, the crude product was purified through column chromatography (of SiO2, 5% EtOAc in hexanes to 10% EtOAc in hexanes) to obtain 13.5 g (90%) 2- phenyl-4- (prop - 1- en-2-yl) pyridine.

15
[ 7379-35-3 ]
[ 98-80-6 ]
[ 57311-18-9 ]

Yield	Reaction Conditions	Operation in experiment
35%	With dipotassium peroxodisulfate; iron(II) acetylacetonate; tetrabutylammomium bromide In dichloromethane; water at 20℃; for 12h;

Reference： [1]Singh, Parvinder Pal; Aithagani, Sravan Kumar; Yadav, Mahipal; Singh, Varun Pratap; Vishwakarma, Ram A. [Journal of Organic Chemistry, 2013, vol. 78, # 6, p. 2639 - 2648]

16
[ 26452-80-2 ]
[ 98-80-6 ]
[ 57311-18-9 ]
[ 42260-39-9 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 7758 - 7763

17
[ 26452-80-2 ]
[ 98-80-6 ]
[ 57311-18-9 ]
[ 26274-35-1 ]
[ 42260-39-9 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 7758 - 7763

18
[ 7379-35-3 ]
[ 98-80-6 ]
[ 57311-18-9 ]
[ 19069-63-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-chlorpyridine hydrochloride In dichloromethane; water for 0.25h; Stage #2: phenylboronic acid With ferrous(II) sulfate heptahydrate; dipotassium peroxodisulfate In dichloromethane; water at 20℃; for 5h; Stage #3: With sodium hydroxide In dichloromethane; water at 20℃; Overall yield = 72 %;	Representative Procedure for the FeSO₄-Mediated Direct Arylation of 4-Cyanopyridine (1a) with PhB(OH)₂ (2a General procedure: TFA (0.75mmol) was added to a DCM/distilled H2O solution(2.5 mL, v/v = 1:1) of 1a (0.5mmol), and then stirred for 15 min. 2a (0.75mmol), K2S2O8 (1.5mmol) were added under air, sequentially an aqueous solution of FeSO4*7H2O in distilled H2O (1.25 mL) was slowly added by syringe pump(10 μL min-1). After complete addition, the reaction mixture was stirred for 5 h at ambient temperature. The mixture was neutralized by NaOH solution (1.0 M), the obtained aqueous phase was extracted with ether. The combined ethereal solution was dried over Na2SO4 and filtered. After evaporating the solvent, the arylated products 2-3aa and 3-3aa were isolated by flash chromatography (hexane:EtOAc = 5:1) in 67% and 27%yields, respectively.

Reference： [1]Komeyama, Kimihiro; Nagao, Yuya; Abe, Manabu; Takaki, Ken [Bulletin of the Chemical Society of Japan, 2014, vol. 87, # 2, p. 301 - 313]

19
[ 57311-18-9 ]
[ 4294-57-9 ]
2-phenyl-4-(p-methylphenyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With Fe<SUB>2</SUB>(O<SUP>t</SUP>Bu)<SUB>6</SUB>; sodium t-butanolate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In tetrahydrofuran at 80℃; for 16h; Glovebox; Inert atmosphere;

Reference： [1]Chua, Yi-Yuan; Duong, Hung A. [Chemical Communications, 2014, vol. 50, # 61, p. 8424 - 8427]

20
[ 26452-80-2 ]
[ 603-33-8 ]
[ 57311-18-9 ]

Yield	Reaction Conditions	Operation in experiment
91%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In N,N-dimethyl acetamide at 90℃; for 4h; Inert atmosphere; Schlenk technique; regioselective reaction;

Reference： [1]Rao, Maddali L.N.; Dhanorkar, Ritesh J. [Tetrahedron, 2015, vol. 71, # 2, p. 338 - 349]

21
[ 26452-80-2 ]
[ 100-59-4 ]
[ 57311-18-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	With chromium dichloride In tetrahydrofuran at 25℃; for 0.25h; Inert atmosphere; chemoselective reaction;

Reference： [1]Steib, Andreas K.; Kuzmina, Olesya M.; Fernandez, Sarah; Malhotra, Sushant; Knochel, Paul [Chemistry - A European Journal, 2015, vol. 21, # 5, p. 1961 - 1965]

22
[ 57311-18-9 ]
chlorobis(cyclooctene)rhodium(I) dimer [ No CAS ]
{Rh(μ-Cl)(4-chloro-2-phenylpyridinato)2}2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	In dichloromethane at 20℃; Inert atmosphere; Schlenk technique;

Reference： [1]Böttcher, Hans-Christian; Graf, Marion; Mayer, Peter [Zeitschrift fur Anorganische und Allgemeine Chemie, 2015, vol. 641, # 11, p. 1856 - 1858]

23
[ 57311-18-9 ]
[ 16419-60-6 ]
2-phenyl-4-(o-tolyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77.4%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ In water; toluene for 16h; Inert atmosphere; Reflux;	23 Synthesis of 2-phenyl-4-(m-tolyl)pyridine 2-methylphenyl boronic acid (6.3 g, 46.40 mmol), 2-phenyl-4-chloropyridine (8.0 g, 42.18 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (692 mg, 1.68 mmol), and potassium phosphate tribasic (29.10 g, 126.54 mmol) 250 mL of toluene and 25 mL of water were placed in a 500 mL round-bottom flask. Nitrogen was bubbled directly into the mixture for 30 min after which tris(dibenzylideneacetone)dipalladium(0) (386 mg, 0.421 mmol) was added. Nitrogen was then bubbled for another 15 minutes then the reaction mixture was heated to reflux for 16 h under nitrogen. The mixture was cooled and the organic layer was separated from the aqueous layer. The organic layer was washed with a saturated brine solution, dried over magnesium sulfate, filtered, and the solvent removed under vacuum to give an off-white solid as the crude. The crude was purified by column chromatography using silica gel as the stationary phase and 2% ethyl acetate in hexanes as the mobile phase. 8.0 g of desired product was obtained after purification (77.4% yield).

Reference： [1]Current Patent Assignee: UNIVERSAL DISPLAY CORP - US2015/307535, 2015, A1 Location in patent: Paragraph 0241

24
[ 15746-57-3 ]
[ 57311-18-9 ]
[ 26042-63-7 ]
[Ru(bpy)2(4-chloro-2-phenylpyridine)][hexafluoridophosphate]*0.5H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65.2%	In dichloromethane for 19h; Reflux;

25
[ 22918-01-0 ]
[ 98-80-6 ]
[ 57311-18-9 ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 5993 - 6000
[2]Journal of Materials Chemistry C,2016,vol. 4,p. 9823 - 9833

26
[ 57311-18-9 ]
[ 73183-34-3 ]
2-(2-phenylpyridin-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane for 72h; Reflux;
	With potassium acetate; palladium diacetate; XPhos In 1,4-dioxane Inert atmosphere; Reflux;	1.1; 3.2; 4.2 step one: A dry 250mL round-bottomed flask was sequentially added 4-chloro-2-phenylpyridine (4.3g, 23.0mmol), pinacol diborate (B2Pin2) (6.1g, 24.0mmol), X-Phos (0.6g, 1.4mmol), palladium acetate (0.2g, 0.9mmol), potassium acetate (3.4g, 34.5mmol) and dioxane 100mL, replaced with N2 three times and heated to reflux under N2 protection and stirred overnight. After the completion of the reaction, it was filtered through diatomaceous earth and anhydrous magnesium sulfate, washed twice with ethyl acetate, and the organic phase was collected and concentrated under reduced pressure to obtain Intermediate 1 (crude product) and used directly in the next step.

Reference： [1]Brunner, Felix; Marinakis, Nathalie; Wobill, Cedric; Willgert, Markus; Ertl, Cathrin D.; Kosmalski, Tatjana; Neuburger, Markus; Bozic-Weber, Biljana; Glatzel, Thilo; Constable, Edwin C.; Housecroft, Catherine E. [Journal of Materials Chemistry C, 2016, vol. 4, # 41, p. 9823 - 9833]
[2]Current Patent Assignee: BEIJING SUMMER SPROUT TECHNOLOGY CO LTD - CN113087745, 2021, A Location in patent: Paragraph 0188-0191; 0211; 0215-0217; 0224; 0228-0230

27
[ 5470-22-4 ]
[ 71-43-2 ]
[ 57311-18-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	With tert-butylhypochlorite; potassium carbonate; at 40℃; for 15h;Schlenk technique;	<strong>[5470-22-4]4-chloropyridine-2-carboxylic acid</strong> (36.9 mg, 0.3 mmol)Potassium carbonate (41.6 mg, 0.3 mmol),And successively adding benzene (5 mL)Tert-butyl hypochlorite (34 [mu] L, 0.3 mmol)To a 25 mL Schlenk reaction flask,And then placed in 40 oil bath reaction 15h.After the reaction,The solvent was removed under reduced pressure,Using petroleum ether / ethyl acetate as the eluent,Silica gel column separation,The yield of 4-Chloro-2-phenylpyridine was 75%.

Reference： [1]Patent: CN106565594,2017,A .Location in patent: Paragraph 0040; 0041; 0042
[2]Organic Letters,2018,vol. 20,p. 7095 - 7099

28
[ 57311-18-9 ]
[ 105-36-2 ]
ethyl 2-(3-(4-chloropyridin-2-yl)phenyl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; mesitylenecarboxylic acid; potassium carbonate In 1,4-dioxane at 120℃; for 15h; Inert atmosphere; Sealed tube; regioselective reaction;

Reference： [1]Paterson, Andrew J.; Heron, Callum J.; McMullin, Claire L.; Mahon, Mary F.; Press, Neil J.; Frost, Christopher G. [Organic and Biomolecular Chemistry, 2017, vol. 15, # 28, p. 5993 - 6000]

29
[ 57311-18-9 ]
[ 86-74-8 ]
9-(2-phenylpyridin-4-yl)-9H-carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 120℃; for 5h; Inert atmosphere;	1.2 Step 2: Synthesis of 9-(2-phenylpyridin-4-yl)-9H-carbazole(abbreviation: HCzppy) next, 12 g of 4-chloro-2-phenylpyridine obtained in the above Step 1, 13 g of 9H-carbazole, and 11 g of sodium-tert-butoxide(abbreviation: tert-BuONa)the flask was placed in a three-necked flask equipped with a reflux tube,The inside of the flask was purged with nitrogen. Further, 280 mL of toluene, 1.3 g of tri-tert-butylphosphine, Tris(dibenzylideneacetone)dipalladium(0) (Abbreviation: Pd 2 (dba) 3) was added thereto,And the mixture was heated and stirred at 120 °C. for 5 hours. The obtained reaction product was filtered, the solvent of the filtrate was distilled off, and the residue was purified by silica gel column chromatography using dichloromethane: hexane = 1: 1 as a developing solvent,11 g (yield 53%, yellow oil) of the target compound was obtained.The synthesis scheme of Step 2 is shown in the following (a-2).

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - JP2018/52929, 2018, A Location in patent: Paragraph 0304; 0308; 0309

30
[ 57311-18-9 ]
[ 1008-89-5 ]

Yield	Reaction Conditions	Operation in experiment
78%	With methanol; magnesium at 20℃;	Experimental section General procedure: The aryl halide was dissolved in 5mL of methanol per mmol of (hetero)arylhalide, magnesium (5 equiv.) added and the mixture was stirred at room temperature. After completion of the reaction (between 6-12h), the reaction mixture was poured into water, acidified with dilute HCl, and extracted with ethyl acetate. The organic phase was dried over MgSO4 and concentrated under reduced pressure. The product was purified if necessary by column chromatography on silica gel.

Reference： [1]Jouha, Jabrane; Khouili, Mostafa; Hiebel, Marie-Aude; Guillaumet, Gérald; Suzenet, Franck [Tetrahedron Letters, 2018, vol. 59, # 32, p. 3108 - 3111]

31
[ 626-61-9 ]
[ 98-80-6 ]
[ 57311-18-9 ]

Yield	Reaction Conditions	Operation in experiment
	With dipotassium peroxodisulfate; silver nitrate; trifluoroacetic acid In dichloromethane; water at 20℃; for 15h;

Reference： [1]Yin, Changzhen; Zhong, Kangbao; Li, Wenjing; Yang, Xiao; Sun, Rui; Zhang, Chunchun; Zheng, Xueli; Yuan, Maolin; Li, Ruixiang; Lan, Yu; Fu, Haiyan; Chen, Hua [Advanced Synthesis and Catalysis, 2018, vol. 360, # 20, p. 3990 - 3998]

32
[ 57311-18-9 ]
[ 124-40-3 ]
[ 37941-27-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	at 140℃; for 24h;

33
[ 110-91-8 ]
[ 57311-18-9 ]
[ 131814-36-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	at 140℃; for 24h;

34
[ 57311-18-9 ]
[ 1026055-99-1 ]

Yield	Reaction Conditions	Operation in experiment
	With 3-chloro-benzenecarboperoxoic acid In chloroform at 0 - 20℃;	3.1 General procedure for the synthesis of substrates General procedure: To a stirred solution of N-heteroaromatic compounds in chloroform (0.5 M) was added meta-chloroperoxybenzoic acid (m-CPBA) (2.0 eq) in portions at 0 °C. After the completion of this course, the reaction mixture was allowed up to room temperature and stirred overnight. An aqueous solution of saturated K2CO3 was added to the mixture to neutralize residual m-CPBA. The resulting mixture was extracted with CHCl3 and isopropanol (volume ratio = 9:1) three times (3 x 30 mL). The organic phase were combined and washed with saturated NaCl solution (30 mL). The organic layer was dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure to give crude products, which were purified by column chromatography. The new products were characterized by 1H NMR, 13C NMR and HRMS.

Reference： [1]Gao, Xianying; Geng, Yang; Han, Shuaijun; Liang, Apeng; Li, Jingya; Zou, Dapeng; Wu, Yangjie; Wu, Yusheng [Tetrahedron Letters, 2018, p. 1551 - 1554]

35
[ 57311-18-9 ]
[ 53293-51-9 ]
2-phenyl-4-(pyrrolidin-1-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	In N,N-dimethyl-formamide at 80℃; Inert atmosphere;

Reference： [1]Kinens, Artis; Balkaitis, Simonas; Suna, Edgars [Journal of Organic Chemistry, 2018, vol. 83, # 20, p. 12449 - 12459]

36
[ 57311-18-9 ]
[ 506-59-2 ]
[ 37941-27-8 ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: 4-chloro-2-phenyl-pyridine; N,N-dimethylammonium chloride With sodium hydroxide In water; N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: With potassium carbonate In water; N,N-dimethyl-formamide at 130℃; for 10h; Sealed tube;	2.2.2. Synthesis of dmappy 4-chloro-2-phenylpyridine (2.8 g, 15 mmol), dimethyllamine hydrochloride (12.2 g, 150 mmol) and sodium hydroxide (6.0 g,150 mmol) were dissolved in DMF/H2O (50/25 mL). The mixture was stirred at room temperature for 30 min and then potassium carbonate (4.1 g, 30 mmol) was added. The mixture was further stirred at 130 °C for 10 h in a sealed tube. After being cooled to room temperature, the mixture was extracted with CH2Cl2 (80 mL). The organic phase was washed with brine, dried over anhydrous Na2SO4 and purified by column chromatography on silica gel with CH2Cl2/CH3OH (50:1) as the eluent, yielding a white solid (2.4 g, 12.1 mmol). Yield: 81%. 1H NMR (CDCl3, 500 MHz, δ [ppm]): 8.37 (d, J=6.4 Hz, 1H), 8.00-7.94 (m,2H), 7.53-7.42 (m, 3H), 6.89 (d, J=2.6 Hz, 1H), 6.56 (dd, J=6.5,2.5 Hz, 1H), 3.15 (s, 6H). HRMS (ESI, m/z): 199.1215 [M+H]+ (calc. 199.1230).

Reference： [1]Meng, Xianwen; Bai, Rubing; Wang, Xiaoxiang; Pan, FangFang; He, Lei [Dyes and Pigments, 2019, vol. 165, p. 458 - 466]

37
[ 57311-18-9 ]
[ 558-17-8 ]
2-(3-(tert-butyl)phenyl)-4-chloropyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; water; potassium acetate In 2-methyltetrahydrofuran at 28 - 30℃; for 24h; Inert atmosphere; Irradiation; Sealed tube;

Reference： [1]Sagadevan, Arunachalam; Greaney, Michael F. [Angewandte Chemie - International Edition, 2019, vol. 58, # 29, p. 9826 - 9830][Angew. Chem., 2019, vol. 131, # 29, p. 9931 - 9935,5]

38
[ 22918-03-2 ]
[ 71-43-2 ]
[ 57311-18-9 ]

Yield	Reaction Conditions	Operation in experiment
70%	With N-methyl-o-aminobenzyl alcohol; potassium <i>tert</i>-butylate at 100℃; for 24h; Sealed tube;

Reference： [1]Chen, Suqing; Chen, Wenjun; Chen, Yu; Liu, Zhenghui; Mu, Tiancheng; Wang, Peng; Yan, Zhenzhong [RSC Advances, 2020, vol. 10, # 25, p. 14500 - 14509]

39
[ 26452-80-2 ]
[ 24388-23-6 ]
[ 57311-18-9 ]
[ 26274-35-1 ]
[ 42260-39-9 ]

Reference： [1]Journal of Organic Chemistry,2020,vol. 85,p. 6498 - 6508
[2]Journal of Organic Chemistry,2020,vol. 85,p. 6498 - 6508
[3]Journal of Organic Chemistry,2020,vol. 85,p. 6498 - 6508
[4]Journal of Organic Chemistry,2020,vol. 85,p. 6498 - 6508
[5]Journal of Organic Chemistry,2020,vol. 85,p. 6498 - 6508

40
[ 26452-80-2 ]
[ 24388-23-6 ]
[ 57311-18-9 ]
[ 26274-35-1 ]

Yield	Reaction Conditions	Operation in experiment
1: 80 %Chromat. 2: 18 %Chromat.	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,4-dioxane; water at 100℃; Inert atmosphere;

Reference： [1]Chen, Jing; Ding, Yechun; He, Chen; Hu, Xin; Huang, Qitong; Kuang, Ying; Liu, Jinbiao; Yang, Min [Journal of Organic Chemistry, 2020, vol. 85, # 10, p. 6498 - 6508]

41
diphenyl(2-phenylpyridin-4-yl)(6-(trifluoromethyl)pyridin-3-yl)phosphonium trifluoromethanesulfonate [ No CAS ]
[ 57311-18-9 ]

Yield	Reaction Conditions	Operation in experiment
70 %Chromat.	With lithium chloride In 1,4-dioxane at 80℃; for 24h; Inert atmosphere; Sealed tube; regioselective reaction;

Reference： [1]Alegre-Requena, Juan V.; Levy, Jeffrey N.; Liu, Renrong; McNally, Andrew; Paton, Robert S. [Journal of the American Chemical Society, 2020, vol. 142, # 25, p. 11295 - 11305]

42
[ 57311-18-9 ]
[ 883107-56-0 ]

Yield	Reaction Conditions	Operation in experiment
42%	With tetramethylammonium fluoride In dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere; Sealed tube;

Reference： [1]Bland, Douglas C.; Lee, So Jeong; Morales-Colón, Mariá T.; Sanford, Melanie S.; Scott, Peter J. H.; See, Yi Yang [Organic Letters, 2021, vol. 23, # 11, p. 4493 - 4498]

43
[ 57311-18-9 ]
C₁₄H₁₀BrNO₂ [ No CAS ]
[ 64-19-7 ]
(8-(4-bromophenyl)-1-(4-chloropyridin-2-yl)-5-hydroxy-9,10-dihydrophenanthren-9-yl)methyl acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27.3%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate at 100℃; for 8h; Inert atmosphere;	4.1.3. General procedures for the synthesis of B1eB20 General procedure: The synthesis of the compounds B1eB20 was previously reportedin ref. 37.Reactions were carried out with Phenylpyridine analogs(0.4 mmol),1,6-enynes (60 mg, 0.2 mmol), [Cp*RhCl2]2 (8 mg, 5 mol%), NaBArF4 (55 mg, 24 mol %) in CH3COOH (1.0 mL) under nitrogenatmosphere, The mixturewas stirred at 100 C for about 8 h and thecompletion of the reaction was monitored by TLC. After cooling toroom temperature, the NaHCO3 aqueous solution was added toadjust the pH to weak alkaline. The mixture was extracted withethyl acetate. The combined organic layers werewashed with brineand the organic phase was dried with anhydrous sodium sulfateand concentrated in vacuo. The crude compound was purified bysilica gel. column chromatography to give corresponding products.

Reference： [1]Zhang, Jian-Wei; Xiong, Yuan; Wang, Feng; Zhang, Fu-Mao; Yang, Xiaodi; Lin, Guo-Qiang; Tian, Ping; Ge, Guangbo; Gao, Dingding [European Journal of Medicinal Chemistry, 2022, vol. 228]

44
[ 21203-86-1 ]
[ 57311-18-9 ]

Yield	Reaction Conditions	Operation in experiment
55%	With pyrylium tetrafluoroborate; magnesium chloride In acetonitrile for 16h; Heating; Sealed tube;	General procedure for the chlorination of amino heteroaromatic compounds General procedure: Unless otherwise specified, an 18 ml screw-capped tube under normal atmosphere is charged with pyrylium tetrafluoroborate 1 (1.5 equiv.) and MgCl2 (2.0 equiv.). The starting material (1.0 equiv.) is then added and directly followed by CH3CN (0.1 M). The resulting mixture is then stirred 5 minutes at 25 °C and then 16 hours at 120 °C. The reaction is allowed to cool to 25 °C. The crude mixture is partitioned between water and EtOAc. The aqueous layer is extracted with EtOAc (3 × 10 ml). The combined organic layers are dried over Na2SO4, concentrated to dryness and purified on silica gel to afford the desired product.

Reference： [1]Ghiazza, Clément; Faber, Teresa; Gómez-Palomino, Alejandro; Cornella, Josep [Nature Chemistry, 2022, vol. 14, # 1, p. 78 - 84]

45
[ 57311-18-9 ]
[ 93756-28-6 ]
2-(2-([1,1'-biphenyl]-2-yl(ethoxy)methyl)phenyl)-4-chloropyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	In toluene at 110℃; for 10h; Schlenk technique; Inert atmosphere;

Reference： [1]Qu, Shuanglin; Tong, Wen-Yan; Wang, Jianbo; Wang, Kang; Yao, Xing-Qi [Organometallics, 2021, vol. 40, # 21, p. 3526 - 3534]

46
[ 123-91-1 ]
[ 57311-18-9 ]
4,4,5,5-tetramethyl-2-(1,1',3,3'-tetrahydro-2,2'-spirobi[inden]-5-yl)-1,3,2-dioxaborolane [ No CAS ]
2-phenyl-4-(1,1',3,3'-tetrahydro-2,2'-spirobi[inden]-5-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate	2.4 2.4 2.4 2-Phenyl-4-(1,1',3,3'-tetrahydro-2,2'-spirobi[inden]-5-yl)pyridine A 250 mL round bottom flask, equipped with a reflux condenser and stir bar, was charged with 4-chloro-2-phenylpyridine (1.896 g, 10.0 mmol, 1.0 equiv), 4,4,5,5-tetramethyl-2-(1,1',3,3'-tetrahydro-2,2'-spirobi[inden]-5-yl)-1,3,2-dioxaborolane (3.81 g, 11.0 mmol, 1.10 equiv), a solution of potassium carbonate (2.76 g, 20.0 mmol, 2.0 equiv) in water (15 mL), and 1,4-dioxane (50 mL). The mixture was sparged with nitrogen for 10 minutes. Palladium(II) acetate (0.112 g, 0.5 mmol, 0.05 equiv) and dicyclohexyl(2',6'-dimethoxy[1,1'-biphenyl]-2-yl)phosphane (SPhos) (0.246 g, 0.6 mmol, 0.06 equiv) were added, sparging continued for 10 minutes then the reaction mixture heated at 100° C. overnight. The reaction mixture was cooled to RT and diluted with ethyl acetate (50 mL) and saturated brine (50 mL). The phases were separated and the aqueous phase extracted with ethyl acetate (50 mL). The combined organic phases were dried over anhydrous sodium sulfate (25 g) and filtered through a pad of silica gel (20 g), eluting with ethyl acetate (100 mL). The filtrate was adsorbed onto Celite (20 g). The crude material was chromatographed on silica gel (300 g), eluting with 0:25:75 to 10:25:75 mixture of ethyl acetate, dichloromethane and heptanes, to give 2-phenyl-4-(1,1',3,3'-tetrahydro-2,2'-spirobi[inden]-5-yl)pyridine as a white solid.

Reference： [1]Current Patent Assignee: UNIVERSAL DISPLAY CORP; BALL SURROUNDING EXHIBITION - US2022/106342, 2022, A1

47
[ 57311-18-9 ]
2-(1',3'-dihydrospiro[fluorene-9,2'-inden]-5'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
4-(1',3'-dihydrospiro[fluorene-9,2'-inden]-5'-yl)-2-phenylpyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate	4-(1',3'-Dihydrospiro[fluorene-9,2'-inden]-5'-yl)-2-phenylpyridine 4-(1',3'-Dihydrospiro[fluorene-9,2'-inden]-5'-yl)-2-phenylpyridine A mixture of 4-chloro-2-phenylpyridine (2.31 g, 12.18 mmol, 1.0 equiv), 2-(1',3'-dihydrospiro[fluorene-9,2'-inden]-5'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxa-borolane (4.80 g, 12.18 mmol, 1.0 equiv) and potassium carbonate (1.683 g, 12.18 mmol, 2.0 equiv) in 1,4-dioxane (50 mL) and water (10 mL) was sparged with nitrogen for 15 minutes. Palladium(II) acetate (0.082 g, 0.365 mmol. 0.03 equiv) and dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphane (SPhos) (0.30 g, 0.730 mmol, 0.06 equiv) were added, sparging continued for 10 minutes then the reaction mixture was heated at reflux for 1.5 hours. LCMS analysis indicated that starting material was consumed. The cooled reaction mixture was diluted with water (20 mL). The suspension was filtered and the solid washed with water (2*5 mL) to give crude 4-(1',3'-dihydrospiro[fluorene-9,2'-inden]-5'-yl)-2-phenylpyridine.
	With dicyclohexyl({2’,6’-dimethoxy-[1,1‘-biphenyl]-2-yl})phosphane; palladium diacetate; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate for 1.5h; Inert atmosphere; Reflux;	1.2 4-(1',3'-Dihydrospiro[fluorene-9,2'-inden]-5'-yl)-2-phenylpyridine 4-(1',3'-Dihydrospiro[fluorene-9,2'-inden]-5'-yl)-2-phenylpyridine A mixture of 4-chloro-2-phenylpyridine (2.31 g, 12.18 mmol, 1.0 equiv), 2-(1',3'-dihydrospiro[fluorene-9,2'-inden]-5'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxa-borolane (4.80 g, 12.18 mmol, 1.0 equiv) and potassium carbonate (1.683 g, 12.18 mmol, 2.0 equiv) in 1,4-dioxane (50 mL) and water (10 mL) was sparged with nitrogen for 15 minutes. Palladium(II) acetate (0.082 g, 0.365 mmol. 0.03 equiv) and dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphane (SPhos) (0.30 g, 0.730 mmol, 0.06 equiv) were added, sparging continued for 10 minutes then the reaction mixture was heated at reflux for 1.5 hours. LCMS analysis indicated that starting material was consumed. The cooled reaction mixture was diluted with water (20 mL). The suspension was filtered and the solid washed with water (2*5 mL) to give crude 4-(1',3'-dihydrospiro[fluorene-9,2'-inden]-5'-yl)-2-phenylpyridine.

Reference： [1]Current Patent Assignee: UNIVERSAL DISPLAY CORP; BALL SURROUNDING EXHIBITION - US2022/106342, 2022, A1
[2]Current Patent Assignee: UNIVERSAL DISPLAY CORP; BALL SURROUNDING EXHIBITION - US2022/106342, 2022, A1 Location in patent: Paragraph 0211; 0213

48
[ 57311-18-9 ]
[ 3389-54-6 ]
(R)-phenyl(2-(2-phenylpyridin-4-yl)pyrrolidin-1-yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: phenyl(pyrrolidine-1-yl)methanone With nickel(II) chloride ethylene glycol dimethyl ether complex; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-κN1,κN1′]bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC]iridium hexafluorophosphate; C₃₈H₅₄N₄; sodium salt of phosphorous acid In Isopropyl acetate at 20℃; for 0.5h; Inert atmosphere; Glovebox; Stage #2: 4-chloro-2-phenylpyridine In Isopropyl acetate at 20℃; for 24h; Inert atmosphere; Irradiation; enantioselective reaction;

Reference： [1]Huo, Haohua; Lin, Yanmei; Qin, Xiao; Shu, Xiaomin; Zhong, De [Journal of the American Chemical Society, 2022]

49
[ 57311-18-9 ]
[ 3389-54-6 ]
C₂₂H₂₀N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: phenyl(pyrrolidine-1-yl)methanone With nickel(II) chloride ethylene glycol dimethyl ether complex; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-κN1,κN1′]bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC]iridium hexafluorophosphate; C₃₈H₅₄N₄; sodium salt of phosphorous acid In Isopropyl acetate at 20℃; for 0.5h; Inert atmosphere; Glovebox; Stage #2: 4-chloro-2-phenylpyridine In Isopropyl acetate at 20℃; for 24h; Inert atmosphere; Irradiation; enantioselective reaction;

Reference： [1]Huo, Haohua; Lin, Yanmei; Qin, Xiao; Shu, Xiaomin; Zhong, De [Journal of the American Chemical Society, 2022]

50
[ 57311-18-9 ]
4,4,5,5-tetramethyl-2-(1,1',3,3'-tetrahydro-2,2'-spirobi[inden]-5-yl)-1,3,2-dioxaborolane [ No CAS ]
2-phenyl-4-(1,1',3,3'-tetrahydro-2,2'-spirobi[inden]-5-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dicyclohexyl({2’,6’-dimethoxy-[1,1‘-biphenyl]-2-yl})phosphane; palladium diacetate; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 100℃;	2.4 2.4 2-Phenyl-4-(1,1',3,3'-tetrahydro-2,2'-spirobi[inden]-5-yl)pyridine A 250 mL round bottom flask, equipped with a reflux condenser and stir bar, was charged with 4-chloro-2-phenylpyridine (1.896 g, 10.0 mmol, 1.0 equiv), 4,4,5,5-tetramethyl-2-(1,1',3,3'-tetrahydro-2,2'-spirobi[inden]-5-yl)-1,3,2-dioxaborolane (3.81 g, 11.0 mmol, 1.10 equiv), a solution of potassium carbonate (2.76 g, 20.0 mmol, 2.0 equiv) in water (15 mL), and 1,4-dioxane (50 mL). The mixture was sparged with nitrogen for 10 minutes. Palladium(II) acetate (0.112 g, 0.5 mmol, 0.05 equiv) and dicyclohexyl(2',6'-dimethoxy[1,1'-biphenyl]-2-yl)phosphane (SPhos) (0.246 g, 0.6 mmol, 0.06 equiv) were added, sparging continued for 10 minutes then the reaction mixture heated at 100° C. overnight. The reaction mixture was cooled to RT and diluted with ethyl acetate (50 mL) and saturated brine (50 mL). The phases were separated and the aqueous phase extracted with ethyl acetate (50 mL). The combined organic phases were dried over anhydrous sodium sulfate (25 g) and filtered through a pad of silica gel (20 g), eluting with ethyl acetate (100 mL). The filtrate was adsorbed onto Celite (20 g). The crude material was chromatographed on silica gel (300 g), eluting with 0:25:75 to 10:25:75 mixture of ethyl acetate, dichloromethane and heptanes, to give 2-phenyl-4-(1,1',3,3'-tetrahydro-2,2'-spirobi[inden]-5-yl)pyridine as a white solid.

Reference： [1]Current Patent Assignee: UNIVERSAL DISPLAY CORP; BALL SURROUNDING EXHIBITION - US2022/106342, 2022, A1 Location in patent: Paragraph 0221

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Technical Information

• Acid-Catalyzed α -Halogenation of Ketones • Addition of a Hydrogen Halide to an Internal Alkyne • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alkyl Halide Occurrence • Alkylation of an Alkynyl Anion • An Alkane are Prepared from an Haloalkane • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Chichibabin Reaction • Chloroalkane Synthesis with SOCI2 • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Conversion of Amino with Nitro • Convert Haloalkanes into Alcohols by SN2 • Deprotonation of Methylbenzene • Directing Electron-Donating Effects of Alkyl • Electrophilic Chloromethylation of Polystyrene • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation of Benzene with Haloalkanes • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Alkenes • Halogenation of Benzene • Hantzsch Pyridine Synthesis • Hiyama Cross-Coupling Reaction • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Methylation of Ammonia • Nitration of Benzene • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Preparation of Alkylbenzene • Preparation of Amines • Pyridines React with Grignard or Organolithium Reagents • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reductive Removal of a Diazonium Group • Reverse Sulfonation——Hydrolysis • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Sulfonation of Benzene • Suzuki Coupling • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Nitro Group Conver to the Amino Function • Vilsmeier-Haack Reaction

Historical Records

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[ 57311-18-9 ]

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[ CAS No. 57311-18-9 ] {[proInfo.proName]}

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[ 57311-18-9 ] Synthesis Path-Downstream 1~50

Technical Information

Related Functional Groups of [ 57311-18-9 ]

Aryls

Chlorides

Related Parent Nucleus of [ 57311-18-9 ]

Pyridines

Precautionary Statements-General

Prevention

Response

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Health hazards

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Related Functional Groups of
[ 57311-18-9 ]

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[ 57311-18-9 ]