[ CAS No. 58254-76-5 ] {[proInfo.proName]}

Name: 58254-76-5|5-Chloro-2-phenylpyridine|97%
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SKU: A985270
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Quality Control of [ 58254-76-5 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 58254-76-5 ]

CAS No. :	58254-76-5	MDL No. :	MFCD04114185
Formula :	C₁₁H₈ClN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UCMPFHHXFOSHSE-UHFFFAOYSA-N
M.W :	189.64	Pubchem ID :	2762866
Synonyms :

Safety of [ 58254-76-5 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362	UN#:
Hazard Statements:	H315-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 58254-76-5 ]

* 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 [ 58254-76-5 ]

[ 58254-76-5 ] Synthesis Path-Downstream 1~50

1
[ 16110-09-1 ]
[ 98-80-6 ]
[ 58254-76-5 ]

Yield	Reaction Conditions	Operation in experiment
83%
83%	With sodium carbonate In ethanol; toluene for 24h; Heating;
75%	With sodium carbonate In ethanol; water; toluene for 3h; Reflux;	62.A Preparation of Compound 62A62AStep A - Preparation of 5-Chloro-2-phenylpyridineA 100~mL, round-bottomed flask, fitted with a reflux condenser was charged with 2,5- dichloropyridine (LOO g, 6.76 mmol), phenylboronic acid (1.07 g, 8.78 mmol), [1,4- bis(diphenylphosphino)butane]palladium(n) dichloride (0.204 g, 0.338 mmol), argon-degassed toluene/ethanol (4: 1, 17 mL) and argon-degassed aqueous 1 N sodium carbonate (6.6 mL). The mixture was heated to reflux for 3 h, cooled to room temperature and diluted with water (15 mL) and EtOAc (100 mL). The layers separated and the aqueous phase was extracted with EtOAc (100 mL). The combine organic extracts were dried over Na2S04, filtered and concentrated. Purification by flash column chromatography (silica gel, 50:50 hexanes/CH2Cl2) provided 5-chloro-2-phenylpyridine (0.959 g, 75%) as a white solid.

73%	In 1,2-dimethoxyethane; water	Synthesis of 5-chloro-2-phenylpyridine Synthesis of 5-chloro-2-phenylpyridine 2,5-Dichloropyridine (30 g, 203 mmol), phenylboronic acid (24.72 g, 203 mmol) and potassium carbonate (84 g, 608 mmol) were added to dimethoxyethane (500 mL) and water (100 mL). The reaction mixture was degassed with nitrogen for 20 min, and Pd(PPh3)4 (2.3 g, 2.0 mmol) was added and reaction mixture was allowed to reflux for 18 h. The reaction was cooled to room temperature, the aqueous layer removed and dimethoxyethane was concentrated to dryness by rotary evaporation under vacuum. The residue was dissolved in DCM and passed through a silica gel plug, eluting with DCM. The solvent was removed and the crude product was chromatographed on silica with 40/60 (v/v) DCM/hexane to 50/50 (v/v) DCM/hexane to yield 28 g (73%) of the product as a white solid (HPLC purity: 99.7%).
73%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,2-dimethoxyethane; water for 18h; Inert atmosphere; Reflux;	synthesis of 5-chloro-2-phenyl pyridine 2,5-dichloro pyridine (30 g, 203 mmol), phenyl Acid (24.72 g, 203 mmol) and potassium carbonate (84 g, 608 mmol) is added to the dimethoxy ethane (500 ml) with water (100 ml) in. Degassing the nitrogen reaction mixture 20 min, and add Pd (PPh3)4(2.3 g, 2.0 mmol) and the reaction mixture is reflux 18 h. The reactant was cooled to the room temperature, and the water is removed by rotary evaporation under vacuum the dimethoxy ethane concentration to drying. The residue is dissolved in DCM by silicon rubber plug, and, for the dissolving DCM. The silicon dioxide is removed in the solvent and the DCM/hexane to the 40/60(v/v) the 50/50(v/v) DCM/hexane chromatography of the crude product, to obtain 28 g (73%) of a white solid product (HPLC purity: 99.7%).
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; water; toluene at 80℃; for 24h;

Reference： [1]Mitchell, M. B.; Wallbank, P. J. [Tetrahedron Letters, 1991, vol. 32, # 20, p. 2273 - 2276]
[2]Ali; McKillop; Mitchell; Rebelo; Wallbank [Tetrahedron, 1992, vol. 48, # 37, p. 8117 - 8126]
[3]Current Patent Assignee: MERCK & CO INC - WO2011/79000, 2011, A1 Location in patent: Page/Page column 62
[4]Current Patent Assignee: UNIVERSAL DISPLAY CORP - US2013/26452, 2013, A1 Location in patent: Page/Page column
[5]Current Patent Assignee: UNIVERSAL DISPLAY CORP - TWI523860, 2016, B Location in patent: Page/Page column 91
[6]Location in patent: scheme or table Brumfield, Stephanie; Matasi, Julius J.; Tulshian, Deen; Czarniecki, Michael; Greenlee, William; Garlisi, Charles; Qiu, Hongchen; Devito, Kristine; Chen, Shu-Cheng; Sun, Yongliang; Bertorelli, Rosalia; Ansell, Justin; Geiss, William; Le, Van-Duc; Martin, Gregory S.; Vellekoop, Samuel A.; Haber, James; Allard, Melissa L. [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 24, p. 7287 - 7290]

2
[ 40473-01-6 ]
[ 108-86-1 ]
[ 58254-76-5 ]

Yield	Reaction Conditions	Operation in experiment
53%	With hexamethyldistannane In 1,4-dioxane for 18h; Heating;

Reference： [1]Zhang; Thomas; Wu [Journal of Organic Chemistry, 2001, vol. 66, # 4, p. 1500 - 1502]

3
[ 16110-09-1 ]
[ 201230-82-2 ]
[ 98-80-6 ]
[ 91-02-1 ]
[ 58254-76-5 ]
(5-chloropyridin-2-yl)(phenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2,5 dichloropyridine With caesium carbonate; 1,3-bis(mesityl)imidazolium chloride In 1,4-dioxane at 80℃; for 0.666667h; Stage #2: carbon monoxide; phenylboronic acid In 1,4-dioxane at 100℃; for 23h;
	With caesium carbonate; 1,3-bis(mesityl)imidazolium chloride In 1,4-dioxane for 23h;

Reference： [1]Maerten, Eddy; Hassouna, Fatima; Couve-Bonnaire, Samuel; Mortreux, André; Carpentier, Jean-François; Castanet, Yves [Synlett, 2003, # 12, p. 1874 - 1876]
[2]Maerten, Eddy; Sauthier, Mathieu; Mortreux, André; Castanet, Yves [Tetrahedron, 2007, vol. 63, # 3, p. 682 - 689]

4
[ 108-86-1 ]
[ 652148-91-9 ]
[ 58254-76-5 ]

Reference： [1]Tetrahedron,2003,vol. 59,p. 10043 - 10049

5
[ 58254-76-5 ]
[ 51934-41-9 ]
[ 594-19-4 ]
[ 480390-54-3 ]

Yield	Reaction Conditions	Operation in experiment
58%	In tetrahydrofuran; pentane	1 Example 1 Example 1 To a solution (50 ml) of 5-chloro-2-phenylpyridine (3.50 g) in tetrahydrofuran was added dropwise t-butyl lithium (1.7 M solution in pentane, 12.0 ml) under an argon atmosphere at -78°C, and the mixture was stirred for 1 hr. To this mixed solution was added a solution (15 ml) of zinc chloride (3.00 g) in tetrahydrofuran, and the mixture was stirred at 0°C for 30 min. Then, ethyl 4-iodobenzoate (3.4 ml) and tetrakis (triphenylphosphine)palladium (1.15 g) were added. This mixture was stirred overnight at room temperature under an argon atmosphere, and poured into 0.5 M hydrochloric acid. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1, volume ratio). Recrystallization from hexane-ethyl acetate gave ethyl 4-(3-chloro-6-phenyl-2-pyridyl)benzoate (3.86 g, yield 58%) as colorless crystals. melting point: 81-82°C.

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP1405636, 2004, A1

6
[ 58254-76-5 ]
[ 33513-42-7 ]
[ 342024-54-8 ]

Yield	Reaction Conditions	Operation in experiment
43%	Stage #1: 5-chloro-2-phenylpyridine With tert.-butyl lithium In tetrahydrofuran at -78℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78 - 20℃; for 1h; Stage #3: With sodium tetrahydroborate In tetrahydrofuran; methanol at 20℃; for 1h;	105 Reference Example 105 tert-Butyl Lithium (1.7M pentane solution, 15 ml) was added slowly to a solution of 5-chloro-2-phenylpyridine (4.70 g) in tetrahydrofuran (50 ml) at -78°C under a nitrogen atmosphere, which was stirred for 1 hour. N,N-Dimethylformamide (2.3 ml) was added to the mixture slowly, which was stirred for 1 hour while raising the temperature to room temperature. After addition of dilute hydrochloric acid the mixture was stirred at room temperature for 30 minutes.The reaction mixture was neutralized with saturated aqueous sodium bicarbonate solution, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. Sodium borohydride (946 mg) was added slowly to a mixture of the residue, tetrahydrofuran (50 ml) and methanol (50 ml) at room temperature, which was stirred for 1 hour. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain 3-chloro-6-phenyl-2-pyridylmethanol (2.35 g, yield 43%) as pale yellow crystals from the fraction eluted with ethyl acetate-hexane (1:6, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 69-70°C

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP1228067, 2004, B1 Location in patent: Page 59-60

7
[ 58254-76-5 ]
[ 51608-60-7 ]
[ 1285665-63-5 ]

Yield	Reaction Conditions	Operation in experiment
70%	With [Cp*Rh(CH₃CN)3][SbF₆]2 In toluene at 90℃; for 48h; Inert atmosphere; Sealed tube; regioselective reaction;

Reference： [1]Li, Yang; Li, Bi-Jie; Wang, Wen-Hua; Huang, Wei-Ping; Zhang, Xi-Sha; Chen, Kang; Shi, Zhang-Jie [Angewandte Chemie - International Edition, 2011, vol. 50, # 9, p. 2115 - 2119]

8
[ 58254-76-5 ]
[ 73183-34-3 ]
2-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With potassium acetate; tricyclohexylphosphine In 1,4-dioxane at 80℃; for 16h; Sealed tube; Inert atmosphere;	62.B Step B - Preparation of Compound 62ΛA 150 mL sealed tube was charged with bis(dibenzylideneacetone)palladium (87 mg, 0.152 mmol), tricyclohexylphosphine (102 mg, 0.364 mmol) and nitrogen-degassed 1 ,4- dioxane (32 mL). After stirring at room temperature for 30 min under nitrogen,bis(pinacolato)diboron (1.41 g, 5.56 mmol), OAc (0.744 g, 7.59 mmol) and 5-chloro-2- phenylpyridine (0.959 g, 5.06 mmol, from Step A) was added to the reaction mixture. The tube was sealed and place in an oil bath at 80 °C for 16 hours. The mixture was cooled to room temperature, diluted with brine (50 mL) and CH2CI2 (100 mL) and the layers were separated. The aqueous phase was extracted with CJ¾C12 (10-0 mL) and the combined organics washed with brine (150 mL), dried over Na2S04, filtered and concentrated. Purification by flash column chromatography (silica gel, 50:50 CH2CI2/EtOAc) provided compound 62A(0.569 g, 40%) as a white solid.
	With potassium acetate; XPhos In 1,4-dioxane at 80℃; for 24h;
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 12h;	1-5 Add 100mmol of M1, 110mmol of pinacol diborate,29.4g potassium acetate (300mmol), 800ml dioxane,And add 1 mol% of dichloro[1,1'-bis(diphenylphosphine)ferrocene]palladium (Pd(dppf)Cl2).React at 100°C for 12h. After the completion of the reaction, the reaction was stopped, and the reactant was cooled to room temperature, water was added, the organic phase was separated, concentrated to obtain a white solid, filtered, and washed with water.The obtained solid was recrystallized and purified with toluene to obtain a white powder M2.Among them, the added amount of Pd(dppf)Cl2 is 1 mol% of M1.

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2011/79000, 2011, A1 Location in patent: Page/Page column 63
[2]Location in patent: scheme or table Brumfield, Stephanie; Matasi, Julius J.; Tulshian, Deen; Czarniecki, Michael; Greenlee, William; Garlisi, Charles; Qiu, Hongchen; Devito, Kristine; Chen, Shu-Cheng; Sun, Yongliang; Bertorelli, Rosalia; Ansell, Justin; Geiss, William; Le, Van-Duc; Martin, Gregory S.; Vellekoop, Samuel A.; Haber, James; Allard, Melissa L. [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 24, p. 7287 - 7290]
[3]Current Patent Assignee: YANTAI XIANHUA CHEM-TECH CO LTD - CN113264871, 2021, A Location in patent: Paragraph 0108-0109; 0111; 0120; 0129; 0137; 0148

9
[ 40473-01-6 ]
[ 100-59-4 ]
[ 58254-76-5 ]

Yield	Reaction Conditions	Operation in experiment
78%	With ferric(III) bromide In tetrahydrofuran; tert-butyl methyl ether at 20℃; for 1.16667h; Inert atmosphere; Schlenk technique;

Reference： [1]Kuzmina, Olesya M.; Steib, Andreas K.; Knochel, Paul; Flubacher, Dietmar [Organic Letters, 2012, vol. 14, # 18, p. 4818 - 4821,4]

10
[ 58254-76-5 ]
[ 126726-62-3 ]
[ 1414972-04-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate monohydrate In water; toluene for 18h; Inert atmosphere; Reflux;	1 Step 1 Synthesis of 2-phenyl-5-(prop-1-en-2-yl)pyridine To a 1 L round bottom flask was added 5-chloro-2-phenylpyridine (10.15 g, 53.5 mmol), dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine (1.8 g, 4.3 mmol), potassium phosphate tribasic monohydrate (37.0 g, 161 mmol) with toluene (200 mL) and water (20 mL). The reaction mixture was degassed with N2 for 20 minutes, then 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (12.07 mL, 64.2 mmol) and Pd2(dba)3 (0.980 g, 1.070 mmol) were added and the reaction mixture was refluxed for 18 h. The aqueous layer was removed and the organic layer was concentrated to dryness. The crude product was chromatographed on silica gel with 0-20% EtOAc in hexane to yield 11 g of the desired product (HPLC purity: 95%). The product was confirmed by GC/MS.
11 g	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium phosphate monohydrate In water; toluene for 18h; Inert atmosphere; Reflux;	synthesis of 2-phenyl-5 - (prop-1-en-2-yl) pyridine 1 L round bottom flask is added 5-chloro-2-phenylpyridin (10.15 g, 53.5 mmol), dicyclohexyl (2 ', 6' -dimethoxy-[ 1,1 '-biphenyl] - 2-yl) diphenylphosphinobiphenyl (1.8 g, 4.3 mmol), mono-hydrated potassium phosphate (37.0 g, 161 mmol) and toluene (200 ml) with water (20 ml). Degassing of the reaction mixture of nitrogen for 20 min. Adding 4, 4, 5, 5-tetramethyl-2 - (prop-1-en-2-yl) - 1, 3, 2- two oxygen boron(12.07 ml, 64.2 mmol) and Pd2(dba)3(0.980 g, 1 . 070 mmol) and reflux the reaction mixture 18 h. Removing the water layer and the concentration of the organic layer to dry. The crude product in the silica gel by 0-20% EtOAc in hexanes solution chromatography, obtaining 11 g of the required product (HPLC purity: 95%). Product confirmed by GC/MS.

Reference： [1]Current Patent Assignee: UNIVERSAL DISPLAY CORP - US2012/299468, 2012, A1 Location in patent: Page/Page column 63
[2]Current Patent Assignee: UNIVERSAL DISPLAY CORP - TWI523860, 2016, B Location in patent: Page/Page column 92

11
[ 58254-76-5 ]
[ 766-47-2 ]
[ 1421006-68-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	With bromopentacarbonylmanganese(I); N-cyclohexyl-cyclohexanamine In diethyl ether at 80℃; for 6h; Inert atmosphere; Schlenk technique; stereoselective reaction;

Reference： [1]Zhou, Bingwei; Chen, Hui; Wang, Congyang [Journal of the American Chemical Society, 2013, vol. 135, # 4, p. 1264 - 1267]

12
[ 657408-07-6 ]
potassium phosphate [ No CAS ]
[ 58254-76-5 ]
[ 126726-62-3 ]
[ 1414972-04-5 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); In hexane; water; toluene;	Synthesis of 2-phenyl-5-(prop-1-en-2-yl)pyridine To a 1 L round bottom flask was added 5-chloro-2-phenylpyridine (10.15 g, 53.5 mmol), dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine (1.8 g, 4.3 mmol), potassium phosphate tribasic monohydrate (37.0 g, 161 mmol) with toluene (200 mL) and water (20 mL). The reaction mixture was degassed with nitrogen for 20 mins. 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (12.07 mL, 64.2 mmol) and Pd2(dba)3 (0.980 g, 1.070 mmol) were added and the reaction mixture was refluxed for 18 h. The aqueous layer was removed and the organic layer was concentrated to dryness. The crude product was chromatographed on silica gel with 0-20% EtOAc in hexane to yield 11 g of the desired product (HPLC purity: 95%). The product was confirmed by GC/MS.

Reference： [1]Patent: US2013/26452,2013,A1 .Location in patent: Page/Page column

13
[ 58254-76-5 ]
[ 925-90-6 ]
[ 66562-61-6 ]

Yield	Reaction Conditions	Operation in experiment
19%	In tetrahydrofuran; water	Synthesis of 5-ethyl-2-phenylpyridine Synthesis of 5-ethyl-2-phenylpyridine 5-Chloro-2-phenylpyridine (16 g, 84 mmol) and Ni(dppe)Cl2 (0.891 g, 1.687 mmol) were added to 300 mL of THF and the reaction mixture was degassed with nitrogen for 20 min. before being cooled to 0° C. Ethylmagnesium bromide (169 mL, 169 mmol) was added dropwise over a period of 60 min. and the reaction mixture stirred for and additional 3 h at before warming to room temperature overnight. The reaction mixture was recooled to 0° C. and quenched with 250 mL of water, extracted with EtOAc and the organic layer dried over sodium sulfate and filtered. The crude material was chromatographed on silica with 95/5 hexane/EtOAc to give 2.9 g (19%) of 5-ethyl-2-phenylpyridine as a white solid.
19%	With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	synthesis of 5-ethyl-2-phenyl pyridine 5-chloro-2-phenylpyridin (16 g, 84 mmol) with Ni (dppe) Cl2(0.891 g, 1 . 687 mmol) is added to 300 ml THF and degassing of the reaction mixture of nitrogen for 20 min, then cooling to 0 °C. The 60 min time added dropwise ethyl magnesium bromide (169 ml, 169 mmol) stirring the reaction mixture and 3 h, subsequently warm to room temperature overnight. Then the reaction mixture cooled to 0 °C and 250 ml water quenching, EtOAc extraction and organic layer for the sodium sulfate drying and filtering. The coarse material for the silicon dioxide of the 95/5 hexane/EtOAc of chromatography, to obtain 2.9 g (19%) of white solid is 5-ethyl-2-phenyl-pyridine.

Reference： [1]Current Patent Assignee: UNIVERSAL DISPLAY CORP - US2013/26452, 2013, A1 Location in patent: Page/Page column
[2]Current Patent Assignee: UNIVERSAL DISPLAY CORP - TWI523860, 2016, B Location in patent: Page/Page column 91; 92

14
[ 58254-76-5 ]
[ 24395-14-0 ]
C₂₆H₂₃ClN₂O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In chlorobenzene at 100℃; for 20h; Schlenk technique;

Reference： [1]Li, Xingwei; Yu, Songjie; Wang, Fen; Wan, Boshun; Yu, Xinzhang [Angewandte Chemie - International Edition, 2013, vol. 52, # 9, p. 2577 - 2580][Angew. Chem., 2013, vol. 125, # 9, p. 2637 - 2640,4]

15
[ 123-91-1 ]
[ 58254-76-5 ]
[ 1441362-53-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With dipotassium peroxodisulfate In water at 80℃; for 12h; Sealed tube; Inert atmosphere; Green chemistry; regioselective reaction;

Reference： [1]Li, Xin; Wang, Hao-Yuan; Shi, Zhang-Jie [New Journal of Chemistry, 2013, vol. 37, # 6, p. 1704 - 1706]

16
[ 58254-76-5 ]
[ 56530-39-3 ]
[ 1446325-86-5 ]

Yield	Reaction Conditions	Operation in experiment
72%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In 1,2-dichloro-ethane at 100℃; for 20h; Inert atmosphere; Sealed tube;

Reference： [1]Yu, Songjie; Wan, Boshun; Li, Xingwei [Organic Letters, 2013, vol. 15, # 14, p. 3706 - 3709]

17
[ 573-57-9 ]
[ 58254-76-5 ]
C₃₁H₂₀ClN [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; Trimethylacetic acid In 1,4-dioxane at 130℃; for 24h; Sealed tube; Inert atmosphere;

Reference： [1]Qi, Zisong; Li, Xingwei [Angewandte Chemie - International Edition, 2013, vol. 52, # 34, p. 8995 - 9000][Angew. Chem., 2013, vol. 125, # 34, p. 9165 - 9170,6]

18
[ 58254-76-5 ]
[ 28035-71-4 ]
C₂₈H₂₁ClN₂O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate In 1,4-dioxane at 120℃; for 24h; Sealed tube; Inert atmosphere; stereoselective reaction;

Reference： [1]Qi, Zisong; Li, Xingwei [Angewandte Chemie - International Edition, 2013, vol. 52, # 34, p. 8995 - 9000][Angew. Chem., 2013, vol. 125, # 34, p. 9165 - 9170,6]

19
[ 58254-76-5 ]
2-(2-azidophenyl)-5-chloropyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With dipotassium peroxodisulfate; copper(l) iodide; benzotriazol-1-yl-sulfonyl azide at 120℃; for 12h; regioselective reaction;
81%	Stage #1: 5-chloro-2-phenylpyridine With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid In acetone at 20℃; for 0.25h; Stage #2: With sodium azide In acetone at 50℃; for 16h; regioselective reaction;
	Stage #1: 5-chloro-2-phenylpyridine With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid In acetone at 20℃; for 0.25h; Schlenk technique; Inert atmosphere; Stage #2: With sodium azide In acetone at 50℃; for 16h; Schlenk technique; Inert atmosphere;

Reference： [1]Azad, Chandra S.; Narula, Anudeep K. [RSC Advances, 2015, vol. 5, # 121, p. 100223 - 100227]
[2]Xie, Fang; Qi, Zisong; Li, Xingwei [Angewandte Chemie - International Edition, 2013, vol. 52, # 45, p. 11862 - 11866][Angew. Chem., 2013, vol. 125, # 45, p. 12078 - 12082,5]
[3]Yu, Yinghua; Chen, Gui; Zhu, Lei; Liao, Yun; Wu, Yufeng; Huang, Xueliang [Journal of Organic Chemistry, 2016, vol. 81, # 18, p. 8142 - 8154]

20
[ 58254-76-5 ]
5-chloro-2-(2-nitrophenyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; [hydroxy(tosyloxy)iodo]benzene; acetic acid; sodium nitrite In acetone at 80℃; for 16h; Sealed tube; Molecular sieve; regioselective reaction;

Reference： [1]Xie, Fang; Qi, Zisong; Li, Xingwei [Angewandte Chemie - International Edition, 2013, vol. 52, # 45, p. 11862 - 11866][Angew. Chem., 2013, vol. 125, # 45, p. 12078 - 12082,5]

21
[ 58254-76-5 ]
[ 886-38-4 ]
C₂₆H₁₈ClNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In dichloromethane at 45℃; for 20h; Inert atmosphere; Sealed tube;

Reference： [1]Yu, Songjie; Li, Xingwei [Organic Letters, 2014, vol. 16, # 4, p. 1220 - 1223]

22
[ 3426-71-9 ]
[ 58254-76-5 ]
[ 1519065-39-4 ]

Yield	Reaction Conditions	Operation in experiment
56%	With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate; silver carbonate In tetrahydrofuran at 100℃; for 10h; Sealed tube;

Reference： [1]Zhou, Bing; Du, Juanjuan; Yang, Yaxi; Feng, Huijin; Li, Yuanchao [Organic Letters, 2014, vol. 16, # 2, p. 592 - 595]

23
[ 58254-76-5 ]
[ 13170-28-0 ]
methyl 4-(2-(5-chloropyridin-2-yl)phenylamino)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate; 1-Adamantanecarboxylic acid In chlorobenzene at 100℃; for 10h; Sealed tube;

Reference： [1]Du, Juanjuan; Yang, Yaxi; Feng, Huijin; Li, Yuanchao; Zhou, Bing [Chemistry - A European Journal, 2014, vol. 20, # 19, p. 5727 - 5731]

24
[ 58254-76-5 ]
[ 4294-57-9 ]
2-phenyl-5-(p-tolyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	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]

25
[ 58254-76-5 ]
[ 1008-89-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 60℃; for 2.5h; Inert atmosphere;	General procedure for the hydrodehalogenation of halogenated heterocycles General procedure: PdCl2(dppf), PdCl2(tbpf) and (A.caPhos)PdCl2. A mixture of the halogenated heterocycle (0.66 mmol) in anhydrous THF (13.2 mL) was degassed by bubbling argon for few minutes. Then, PdCl2(dppf) (27.0 mg, 0.033 mmol, 5.0 mol%), TMEDA (0.130 g, 1.12 mmol, 1.7 equiv) and finally NaBH4 (42.4 mg, 1.12 mmol, 1.7 equiv) were introduced in sequence. The mixture was stirred at room temperature under argon for the proper time and then worked up as described above.

Reference： [1]Chelucci, Giorgio; Figus, Susanna [Journal of Molecular Catalysis A: Chemical, 2014, vol. 393, p. 191 - 209]

26
[ 40473-01-6 ]
[ 603-33-8 ]
[ 58254-76-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium acetate; palladium diacetate; triphenylphosphine In 1-methyl-pyrrolidin-2-one at 110℃; for 2h; Schlenk technique; Inert atmosphere; chemoselective reaction;

Reference： [1]Rao, Maddali L.N.; Dhanorkar, Ritesh J. [European Journal of Organic Chemistry, 2014, vol. 2014, # 24, p. 5214 - 5228]

27
[ 591-50-4 ]
C₅H₃Cl₂MgN [ No CAS ]
[ 58254-76-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: iodobenzene With TurboGrignard In tetrahydrofuran at -40℃; for 1h; Inert atmosphere; Stage #2: With tbepc In tetrahydrofuran at -40 - 0℃; for 2h; Inert atmosphere; Stage #3: C₅H₃Cl₂MgN Further stages;

Reference： [1]Liu, Kun Ming; Liao, Lian Yan; Duan, Xin Fang [Chemical Communications, 2015, vol. 51, # 6, p. 1124 - 1127]

28
[ 16110-09-1 ]
[ 603-33-8 ]
[ 58254-76-5 ]

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]

29
[ 16110-09-1 ]
[ 100-59-4 ]
[ 58254-76-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	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]

30
[ 58254-76-5 ]
[ 573-57-9 ]
C₂₁H₁₆ClNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; oxygen In toluene at 120℃;

Reference： [1]Cheng, Hanchao; Dong, Wanrong; Dannenberg, Carl Albrecht; Dong, Shunxi; Guo, Qianqian; Bolm, Carsten [ACS Catalysis, 2015, vol. 5, # 5, p. 2770 - 2773]

31
[ 58254-76-5 ]
[ 100-52-7 ]
(2-(5-chloropyridin-2-yl)phenyl)(phenyl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With bromopentacarbonylmanganese(I); dimethyl zinc(II); zinc dibromide In 1,2-dichloro-ethane; toluene at 60℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube;

Reference： [1]Zhou, Bingwei; Hu, Yuanyuan; Wang, Congyang [Angewandte Chemie - International Edition, 2015, vol. 54, # 46, p. 13659 - 13663][Angew. Chem., 2015, vol. 127, # 46, p. 13863 - 13867]

32
5-chloropyridine-2-yl fluorosulfonate [ No CAS ]
[ 98-80-6 ]
[ 58254-76-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: 5-chloropyridine-2-yl fluorosulfonate; phenylboronic acid With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In 1,4-dioxane for 0.166667h; Stage #2: With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 24h; chemoselective reaction;

Reference： [1]Zhang, Enxuan; Tang, Jiaze; Li, Suhua; Wu, Peng; Moses, John E.; Sharpless, K. Barry [Chemistry - A European Journal, 2016, vol. 22, # 16, p. 5692 - 5697]

33
[ 924-44-7 ]
[ 58254-76-5 ]
ethyl 3-chloropyrido[2,1-a]isoindole-6-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With silver hexafluoroantimonate; carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; copper diacetate In 1,2-dichloro-ethane at 110℃; for 24h; Inert atmosphere; Sealed tube;

Reference： [1]Chen, Xun; Hu, Xinwei; Deng, Yuanfu; Jiang, Huanfeng; Zeng, Wei [Organic Letters, 2016, vol. 18, # 18, p. 4742 - 4745]

34
[ 50-00-0 ]
[ 58254-76-5 ]
(2-(5-chloropyridin-2-yl)phenyl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; sodium acetate; zinc dibromide In 1,2-dichloro-ethane at 60℃; for 24h; Sealed tube; Inert atmosphere;

Reference： [1]Zhang, Guo-Fu; Li, Yue; Xie, Xiao-Qiang; Ding, Cheng-Rong [Organic Letters, 2017, vol. 19, # 5, p. 1216 - 1219]

35
[ 40473-01-6 ]
[ 98-80-6 ]
[ 58254-76-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	With [Pd(N-(3-chloro-2-quinoxalinyl)-N'-(2,6-diisopropylphenyl)imidazolium)(PPh₃)Cl₂]; potassium carbonate In water at 70℃; for 3h;
82%	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,2-dimethoxyethane; water at 80℃; for 14h; Inert atmosphere;	4.1.1. General procedures for the synthesis of compounds 18a-18e,18j, 18k, 18m-18p, 18r, 18s General procedure: Reactions were carried out with Phenylboronic acid (146 mg,1.2 mmol), 2-bromo-pyridine derivatives (234 mg, 1.0 mmol, 2-bromo-4-phenylpyridine for 18a; 172 mg, 1.0 mmol, 2-bromo-4-methylpyridine for 18b; 192 mg, 1.0 mmol, 2-bromo-4-chloropyridine for 18c; 183 mg, 1.0 mmol, 2-bromoisonicotinonitrilefor 18d; 186 mg, 1.0 mmol, 2-bromoisonicotinaldehyde for 18e;176 mg, 1.0 mmol, 2-bromo-5-fluoropyridine for 18j; 192 mg,1.0 mmol, 2-bromo-5-chloropyridine for 18k; 183 mg, 1.0 mmol, 6-bromonicotinonitrile for 18m; 186 mg, 1.0 mmol, 6-bromonicotinaldehyde for 18n; 236 mg, 1.0 mmol, 2-bromo-5-(methylsulfonyl)pyridine for 18o, 200 mg, 1.0 mmol, 1-(6-bromopyridin-3-yl)ethan-1-one for 18p, 234 mg, 1.0 mmol, 2-bromo-5-phenylpyridine for 18r; 263 mg, 1.0 mmol, N-benzyl-6-bromopyridin-3-amine for 18s), Pd(PPh3)2Cl2 (3.5 mg, 0.5 mol %),K2CO3 (387 mg, 2.8 mmol) in DME/H2O (8 mL, 3:1) under nitrogenatmosphere. The mixture was stirred at 80 C for about 14 h and thecompletion of the reaction was monitored by TLC. After cooling toroomtemperature, themixturewas extracted with ethyl acetate. Thecombined organic layers were washed with brine and the organicphase was dried with anhydrous sodium sulfate and concentrated invacuo. The crude compound was purified by silica gel column chromatographyto give corresponding intermediates.
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; water; toluene for 12h; Reflux; Inert atmosphere;

	With potassium phosphate tribasic heptahydrate; palladium diacetate In water; isopropyl alcohol at 80℃;	Procedure A General procedure: A mixture of 2-bromopyridines (2 mmol), boronic acids (3 mmol), Pd(OAc)2 (6.8 mg, 1.5 mol%), K3PO4·7H2O (1.35 g, 4 mmol) in mixture of isopropanol (10 mL) and water (10 mL) was stirred at 80°C overnight. The mixture was added brine (40 mL) and extracted four times with ethyl acetate (4 x 25 mL), the solvent was evaporated under reduced pressure and the product was isolated by short column chromatography using ethyl acetate and petroleum as eluent.
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; water; toluene for 2h; Schlenk technique; Inert atmosphere; Reflux;
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water at 120℃; for 12h;	6-8 Synthesis Example 6: Synthesis of compound LEM-6 100mmol of 2-bromo-5-chloropyridine, 100mmol of phenylboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water were added to the reaction flask, and 1mol% of Pd(PPh3)4 was added. React at 120°C for 12h. After the completion of the reaction, the reaction was stopped, and the reactant was cooled to room temperature, water was added, and the organic phase was concentrated to obtain a white solid, which was filtered and washed with water. The obtained solid was recrystallized and purified with toluene to obtain a white powder M1. Wherein, the amount of Pd(PPh3)4 added is 1 mol% of 2-bromo-5-chloropyridine.
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water at 120℃; for 12h;	1-5 Synthesis Example 1: Synthesis of Compound A1 Add 100mmol of 2-bromo-5-chloropyridine, 100mmol of phenylboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of tetrahydrofuran (THF) and 200ml of water into the reaction flask, and add 1mol% of tetrakis(triphenylphosphine) ) Palladium (Pd(PPh3)4). React at 120°C for 12h. After the completion of the reaction, the reaction was stopped, the reactant was cooled to room temperature, water was added, and the organic phase was concentrated to obtain a white solid, which was filtered and washed with water. The obtained solid was recrystallized and purified with toluene to obtain a white powder M1. Wherein, the amount of Pd(PPh3)4 added is 1 mol% of 2-bromo-5-chloropyridine.
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; water; toluene for 20h; Inert atmosphere; Reflux;

Reference： [1]Ramakrishna; Dastagiri Reddy [Dalton Transactions, 2017, vol. 46, # 26, p. 8598 - 8610]
[2]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]
[3]Zhang, Guo-Fu; Li, Yue; Xie, Xiao-Qiang; Ding, Cheng-Rong [Organic Letters, 2017, vol. 19, # 5, p. 1216 - 1219]
[4]Zhang, Wei; Li, Zhengkai; Zhang, Yihan; Yang, Li; Zhou, Xiangge [Synthetic Communications, 2017, vol. 47, # 8, p. 793 - 802]
[5]Li, Zhong-Yuan; Li, Liang; Li, Qi-Li; Jing, Kun; Xu, Hui; Wang, Guan-Wu [Chemistry - A European Journal, 2017, vol. 23, # 14, p. 3285 - 3290]
[6]Current Patent Assignee: YANTAI XIANHUA CHEM-TECH CO LTD - CN112939959, 2021, A Location in patent: Paragraph 0136-0138; 0142-0144; 0148-0150
[7]Current Patent Assignee: YANTAI XIANHUA CHEM-TECH CO LTD - CN113264871, 2021, A Location in patent: Paragraph 0108-0110; 0117-0119; 0126-0128; 0134-0136"...
[8]Qu, Shuanglin; Tong, Wen-Yan; Wang, Jianbo; Wang, Kang; Yao, Xing-Qi [Organometallics, 2021, vol. 40, # 21, p. 3526 - 3534]

36
[ 58254-76-5 ]
5-chloro-2-phenylpyridine 1-oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 3-chloro-benzenecarboperoxoic acid In chloroform at 0 - 20℃; for 12h;	Procedure C General procedure: To a stirred solution of 2-phenylpyridines (6 mmol) in CHCl3 (2 mL) was added 70% m-CPBA (1 equiv.), portionwise at 0°C. The resulting mixture was stirred at room temperature for 12 h, at which time complete consumption of starting material was observed by TLC. The reaction mixture was diluted with CHCl3, and solid K2CO3 (4 equiv.) was added. The resulting mixture was stirred for an additional 10 min. The solid was separated by filtration, and the filtrate was dried over Na2SO4 and concentrated under reduced pressure to afford the 2-phenylpyridine N-oxides in yields of 60-85%.

Reference： [1]Zhang, Wei; Li, Zhengkai; Zhang, Yihan; Yang, Li; Zhou, Xiangge [Synthetic Communications, 2017, vol. 47, # 8, p. 793 - 802]

37
[ 58254-76-5 ]
[ 108-88-3 ]
2-(3-benzylphenyl)-5-chloropyridine [ No CAS ]
5-chloro-2-(3,5-dibenzylphenyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 40% 2: 20%	With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; perfluoroisopropyl iodide; 4-chlorobenzaldehyde; sodium carbonate In water at 140℃; for 48h; Schlenk technique; Inert atmosphere;

Reference： [1]Li, Bo; Fang, Sheng-Long; Huang, Dan-Ying; Shi, Bing-Feng [Organic Letters, 2017, vol. 19, # 15, p. 3950 - 3953]

38
5-chloropyridine-2-yl fluorosulfonate [ No CAS ]
[ 28557-00-8 ]
[ 58254-76-5 ]

Yield	Reaction Conditions	Operation in experiment
73%	With cobalt(III) acetylacetonate; nickel diacetate In 1-methyl-pyrrolidin-2-one; benzene at 65℃; for 8h; Inert atmosphere; Schlenk technique;	10 Under a nitrogen atmosphere, 15 mL of a clean, clean Schlenk tube was charged with 5-chloro-2-pyridine fluorosulfonate (1.2.3 mg, 2.0 mmol), Co (acac) 3 (7.2 mg, 0.02 mmol), Ni (OAc) 2 (4.96 mg, 0.02 mmol), N-methyl pyrrolidone (3.0 mL) and phenyl Zinc chloride solution (7.1 mL, 0.35 mol / L, 2.5 mmol). The Schlenk tube was then heated in a 65 ° C oil bath for 8 hours, at which point TLC showed complete reaction of the starting material. The Schlenk tube was then cooled in an ice-water bath and 2.0 mL of purified water was added to the reaction system to carry out the quenching reaction. After stirring at room temperature for 15 minutes, the layers were allowed to stand to obtain an aqueous phase and an organic phase. The aqueous phase was extracted with dichloromethane (3 mL X3). The extracted extract and the organic phase were combined and dried over anhydrous sodium sulfate, and the filtrate was filtered. The filtrate was concentrated and chromatographed on silica gel to give a white solid, 226 mg as a yield of 73%.

Reference： [1]Current Patent Assignee: ASYMCHEM INC. - CN106905227, 2017, A Location in patent: Paragraph 0075-0077

39
[ 16110-09-1 ]
[ 5123-13-7 ]
[ 58254-76-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	With 4'-phenyl-2,2':6',2-terpyridine; potassium methanolate; cobalt(II) chloride In N,N-dimethyl-formamide at 80℃; for 16h; Sealed tube; Inert atmosphere; Glovebox;

Reference： [1]Duong, Hung A.; Wu, Wenqin; Teo, Yu-Yuan [Organometallics, 2017, vol. 36, # 22, p. 4363 - 4366]

40
[ 58254-76-5 ]
[ 308358-34-1 ]
1-(2-(5-chloropyridin-2-yl)phenyl)-5-phenylpentan-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; zinc diacetate In acetone at 80℃; for 12h;

Reference： [1]Xia, Jintao; Huang, Zhipeng; Zhou, Xukai; Yang, Xifa; Wang, Feng; Li, Xingwei [Organic Letters, 2018, vol. 20, # 3, p. 740 - 743]

41
[ 58254-76-5 ]
[ 611-73-4 ]
C₁₈H₁₂ClNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With silver (II) carbonate; sodium persulfate; dodecacarbonyl-triangulo-triruthenium; (1S)-10-camphorsulfonic acid In dichloromethane; tert-butyl methyl ether at 100℃; for 48h; Sealed tube; regioselective reaction;

Reference： [1]Jing, Kun; Li, Zhong-Yuan; Wang, Guan-Wu [ACS Catalysis, 2018, vol. 8, # 12, p. 11875 - 11881]

42
[ 58254-76-5 ]
C₃₁H₂₆BClO₂ [ No CAS ]
C₃₆H₂₂ClN [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; water; toluene for 20h; Reflux; Inert atmosphere;	4 5-chloro-2-phenyl - pyridine (10mmol), 2- boronic acid ester-7-chloro - spiro fluorene (10mmol) andNa2CO3 (80 mmol) was added to toluene/EtOH/H2O (75/25/50, mL) solvent, forming a mixed solution, and then adding Pd(PPh3) 4 (0.48 mmol) to the above mixed solution,The reflux reaction was carried out for 20 hours under a nitrogen atmosphere.The resulting mixture was then cooled to room temperature and extracted with ethyl acetate.The aqueous layer was further extracted with dichloromethane, the combined washed with brine, dried using MgSO4, then filtered and concentrated.The residue was recrystallized from dichloromethane and methanol to afford white solid intermediate ET 22-1.

Reference： [1]Current Patent Assignee: TIANMA MICROELECTRONICS CO., LTD. - CN109503466, 2019, A Location in patent: Paragraph 0082; 0084-0086

43
C₂₂H₁₄Cl₂N₂ [ No CAS ]
[ 58254-76-5 ]

Yield	Reaction Conditions	Operation in experiment
75%	With dichloro(1,5-cyclooctadiene)ruthenium(II); hydrogen In 1,4-dioxane at 130℃; for 18h; Glovebox;

Reference： [1]Zhu, Jun; Chen, Peng-hao; Lu, Gang; Liu, Peng; Dong, Guangbin [Journal of the American Chemical Society, 2019, vol. 141, # 46, p. 18630 - 18640]

44
[ 58254-76-5 ]
[ 81-07-2 ]
C₁₈H₁₁ClN₂O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; [bis(acetoxy)iodo]benzene; sodium acetate In 2,2,2-trifluoroethanol; acetonitrile at 100℃; for 48h; Inert atmosphere; Sealed tube;	2.3. General procedure for synthesis of product 5 or 6 General procedure: Arenes (1/4, 0.2 mmol), 2 (0.3 mmol), PhI(OAc)2 (0.3mmol), [Cp*RhCl2]2 (4 mol%), NaOAc (0.06 mmol), and TFE(1.0 mL), CH3CN (1.0 mL) were charged into a pressure tube.The reaction mixture was stirred at 100 °C for 48 h. After thesolvent was removed under reduced pressure, the residue waspurified by silica gel chromatography using PE/EA (2:1) toafford compound 5/6.

Reference： [1]Gao, Hui; Li, Xingwei; Sun, Jiaqiong; Xu, Youwei; Zheng, Guangfan; Zhou, Xukai [Cuihua Xuebao/Chinese Journal of Catalysis, 2020, vol. 41, # 11, p. 1723 - 1733]

45
[ 58254-76-5 ]
C₁₈H₁₃NO [ No CAS ]
C₄₀H₂₇N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (dibenzylideneacetone)palladium; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 12h;	6 In the reaction flask, 200 mmol of M1, 100 mmol of M2, 28.8 g of sodium tert-butoxide (300 mmol), 800 ml of xylene were added, and 1 mol% of Pd(dba) was added. React at 120°C for 12h. After the completion of the reaction, the reaction was stopped, and the reactant was cooled to room temperature, water was added, filtered, and washed with water. The obtained solid was recrystallized and purified with toluene to obtain white powder LEM-6. Among them, the amount of Pd(dba) added is 1 mol% of M2.

Reference： [1]Current Patent Assignee: YANTAI XIANHUA CHEM-TECH CO LTD - CN112939959, 2021, A Location in patent: Paragraph 0136-0137; 0140-0141

46
[ 58254-76-5 ]
C₁₇H₁₂N₂O [ No CAS ]
C₃₉H₂₆N₄O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (dibenzylideneacetone)palladium; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 12h;	7 In the reaction flask, 200 mmol of M1, 100 mmol of M2, 28.8 g of sodium tert-butoxide (300 mmol), 800 ml of xylene were added, and 1 mol% of Pd(dba) was added. React at 120°C for 12h. After the completion of the reaction, the reaction was stopped, and the reactant was cooled to room temperature, water was added, filtered, and washed with water. The obtained solid was recrystallized and purified with toluene to obtain white powder LEM-7. Among them, the amount of Pd(dba) added is 1 mol% of M2.

Reference： [1]Current Patent Assignee: YANTAI XIANHUA CHEM-TECH CO LTD - CN112939959, 2021, A Location in patent: Paragraph 0142-0143; 0146-0147

47
[ 58254-76-5 ]
C₁₇H₁₂N₂O [ No CAS ]
C₂₈H₁₉N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (dibenzylideneacetone)palladium; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 12h;	8 Add 100mmol of M1, 100mmol of M2, 28.8g of sodium tert-butoxide (300mmol), 800ml of xylene into the reaction flask, and add 1mol% of Pd(dba). React at 120°C for 12h. After the completion of the reaction, the reaction was stopped, and the reactant was cooled to room temperature, water was added, filtered, and washed with water. The obtained solid was recrystallized and purified with toluene to obtain a white powder M3. Among them, the amount of Pd(dba) added is 1 mol% of M2.

Reference： [1]Current Patent Assignee: YANTAI XIANHUA CHEM-TECH CO LTD - CN112939959, 2021, A Location in patent: Paragraph 0148-0149; 0152

48
[ 58254-76-5 ]
C₂₅H₂₇BO₃ [ No CAS ]
C₃₀H₂₃NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water at 120℃; for 12h;	7 100mmol of 2-phenyl-5-chloropyridine, 100mmol of M4, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water were added to the reaction flask, and 1mol% of Pd(PPh3)4 was added. React at 120°C for 12h. After the completion of the reaction, the reaction was stopped, the reactant was cooled to room temperature, water was added, and the organic phase was concentrated to obtain a white solid, which was filtered and washed with water. The obtained solid was recrystallized and purified with toluene to obtain a white powder M5. Among them, the added amount of Pd(PPh3)4 is 1 mol% of M4.

Reference： [1]Current Patent Assignee: YANTAI XIANHUA CHEM-TECH CO LTD - CN113321641, 2021, A Location in patent: Paragraph 0184-0185; 0190

49
[ 58254-76-5 ]
[ 501-65-5 ]
3-chloro-6,7-diphenylpyrido[2,1-a]isoquinolin-5-ium hexafluorophosphate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium hexafluorophosphate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In water at 35℃; for 3.5h; Electrochemical reaction; Green chemistry; regioselective reaction;

Reference： [1]Chen, Jia-Yi; Li, Ming; Li, Rui-Tao; Ma, Qiang; Ni, Shao-Fei; Wang, Zi-Chen; Wen, Li-Rong; Zhang, Lin-Bao [Green Chemistry, 2021, vol. 23, # 23, p. 9515 - 9522]

50
[ 58254-76-5 ]
C₁₄H₁₀BrNO₂ [ No CAS ]
[ 64-19-7 ]
(8-(4-bromophenyl)-1-(5-chloropyridin-2-yl)-5-hydroxy-9,10-dihydrophenanthren-9-yl)methyl acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25.5%	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]

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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

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[ 58254-76-5 ]

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Code	Phrase
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[ CAS No. 58254-76-5 ] {[proInfo.proName]}

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[ 58254-76-5 ] Synthesis Path-Downstream 1~50

Technical Information

Related Functional Groups of [ 58254-76-5 ]

Aryls

Chlorides

Related Parent Nucleus of [ 58254-76-5 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 58254-76-5 ]

Related Parent Nucleus of
[ 58254-76-5 ]