[ CAS No. 15854-87-2 ] {[proInfo.proName]}

Name: 15854-87-2|4-Iodopyridine|98%
Brand: Ambeed
SKU: A103500
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2D 3D

Structure of 15854-87-2 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 15854-87-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 15854-87-2 ]

SDS Specification

Alternatived Products of [ 15854-87-2 ]

Product Details of [ 15854-87-2 ]

CAS No. :	15854-87-2	MDL No. :	MFCD02093937
Formula :	C₅H₄IN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RTLUPHDWSUGAOS-UHFFFAOYSA-N
M.W :	205.00	Pubchem ID :	609492
Synonyms :

Calculated chemistry of [ 15854-87-2 ]

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	36.95
TPSA :	12.89 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.48 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.56
Log Po/w (XLOGP3) :	1.51
Log Po/w (WLOGP) :	1.69
Log Po/w (MLOGP) :	1.41
Log Po/w (SILICOS-IT) :	2.47
Consensus Log Po/w :	1.73

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.7
Solubility :	0.412 mg/ml ; 0.00201 mol/l
Class :	Soluble
Log S (Ali) :	-1.39
Solubility :	8.37 mg/ml ; 0.0408 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.98
Solubility :	0.215 mg/ml ; 0.00105 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.58

Safety of [ 15854-87-2 ]

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

Application In Synthesis of [ 15854-87-2 ]

* 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.

Upstream synthesis route of [ 15854-87-2 ]
Downstream synthetic route of [ 15854-87-2 ]

[ 15854-87-2 ] Synthesis Path-Upstream 1~24

1
[ 110-86-1 ]
[ 15854-87-2 ]

Yield	Reaction Conditions	Operation in experiment
50%	Stage #1: With [(THF)Li(μ-2,2,6,6-tetramethylpiperidide)(μ-tert-butyl)Zn(tert-butyl)] In tetrahydrofuran at 0℃; for 2 h; Inert atmosphere Stage #2: With iodine In tetrahydrofuran at 0℃; for 1 h; Inert atmosphere	General procedure: [Li(TMP)Zn(tBu)₂] 1 was made according to the literature procedure² on a 0.4 mmol scale in THF solution. To this solution pypyridine (0.032 mL, 0.4 mmol) was added at 0°C and the resultant light orange reaction allowed to for 2 hours. Next the solution was quenched with I₂ (508 mg, in 1 mL THF) and allowed to stir for 1 hour. A 10percent solution of Na₂S₂O₃ was added until bleaching and the product extracted with DCM (3 x 1 mL). The combined organic extracts were dried over MgSO₄ and the solvent removed under reduced pressure. The residue was purified by SiO₂ chromatography using EtOAc:Heptane (20:80--->30:70) to give compound 5a as an off white solid 42mg (50percent) ¹H NMR (400 MHz,CDCl₃) δ ppm 7.59 - 7.86 (m, 2 H) 8.07 - 8.44 (m, 2 H).

Reference： [1] Tetrahedron Letters, 2011, vol. 52, # 36, p. 4590 - 4594
[2] Journal of Organic Chemistry, 1984, vol. 49, # 20, p. 3857 - 3859

2
[ 504-24-5 ]
[ 15854-87-2 ]

Reference： [1] Organic Letters, 2007, vol. 9, # 5, p. 891 - 894
[2] Chemistry - A European Journal, 2018, vol. 24, # 55, p. 14622 - 14626
[3] Tetrahedron Letters, 2010, vol. 51, # 52, p. 6839 - 6842
[4] Journal of the Chemical Society, 1953, p. 3226,3229
[5] Synthetic Communications, 1996, vol. 26, # 19, p. 3543 - 3547

3
[ 626-61-9 ]
[ 15854-87-2 ]

Reference： [1] Journal of Organic Chemistry, 2009, vol. 74, # 13, p. 4893 - 4895
[2] Monatshefte fuer Chemie, 1885, vol. 6, p. 315[3] Chemische Berichte, 1885, vol. 18, p. 930
[4] Chemical & Pharmaceutical Bulletin, 1982, vol. 30, # 5, p. 1731 - 1737

4
[ 1120-87-2 ]
[ 15854-87-2 ]

Reference： [1] Tetrahedron, 2000, vol. 56, # 10, p. 1349 - 1360

5
[ 7379-35-3 ]
[ 15854-87-2 ]

Reference： [1] Synlett, 2003, # 12, p. 1801 - 1804
[2] Inorganic Chemistry, 2015, vol. 54, # 12, p. 6055 - 6061

6
[ 19524-06-2 ]
[ 5029-67-4 ]
[ 15854-87-2 ]

Reference： [1] Patent: US6358971, 2002, B1,

7
[ 626-61-9 ]
[ 10034-85-2 ]
[ 15854-87-2 ]

Reference： [1] Monatshefte fuer Chemie, 1885, vol. 6, p. 315[2] Chemische Berichte, 1885, vol. 18, p. 930

8
[ 15854-87-2 ]
[ 7037-49-2 ]

Reference： [1] Tetrahedron Letters, 2017, vol. 58, # 29, p. 2856 - 2858

9
[ 19524-06-2 ]
[ 5029-67-4 ]
[ 15854-87-2 ]

Reference： [1] Patent: US6358971, 2002, B1,

10
[ 15854-87-2 ]
[ 626-64-2 ]

Reference： [1] Chemistry - A European Journal, 2010, vol. 16, # 8, p. 2366 - 2370
[2] Tetrahedron Letters, 2011, vol. 52, # 41, p. 5338 - 5341

11
[ 15854-87-2 ]
[ 108-90-7 ]
[ 5957-96-0 ]
[ 4467-15-6 ]
[ 5957-92-6 ]

Reference： [1] Tetrahedron Letters, 1989, vol. 30, # 26, p. 3433 - 3436

12
[ 15854-87-2 ]
[ 108-95-2 ]
[ 4783-86-2 ]

Reference： [1] Catalysis Science and Technology, 2016, vol. 6, # 6, p. 1701 - 1709
[2] Synlett, 2012, # 1, p. 101 - 106
[3] Tetrahedron Letters, 2006, vol. 47, # 29, p. 5045 - 5048

13
[ 15854-87-2 ]
[ 139-02-6 ]
[ 4783-86-2 ]

Reference： [1] Tetrahedron, 2002, vol. 58, # 24, p. 4931 - 4935

14
[ 15854-87-2 ]
[ 100-51-6 ]
[ 49826-70-2 ]

Reference： [1] Tetrahedron, 2002, vol. 58, # 24, p. 4931 - 4935

15
[ 15854-87-2 ]
[ 111-86-4 ]
[ 64690-19-3 ]

Reference： [1] Journal of the American Chemical Society, 2008, vol. 130, # 20, p. 6586 - 6596

16
[ 188290-36-0 ]
[ 15854-87-2 ]
[ 21298-54-4 ]
[ 21308-82-7 ]

Reference： [1] Heterocycles, 1986, vol. 24, # 3, p. 799 - 803

17
[ 15854-87-2 ]
[ 1692-15-5 ]
[ 1910-42-5 ]

Reference： [1] Patent: CN107935918, 2018, A,

18
[ 2510-22-7 ]
[ 15854-87-2 ]
[ 73564-69-9 ]

Reference： [1] Chemistry - A European Journal, 2011, vol. 17, # 25, p. 7032 - 7040
[2] Tetrahedron Letters, 1999, vol. 40, # 29, p. 5413 - 5416

19
[ 15854-87-2 ]
[ 133810-35-2 ]
[ 73564-69-9 ]

Reference： [1] Journal of the American Chemical Society, 2013, vol. 135, # 33, p. 12228 - 12240

20
[ 15854-87-2 ]
[ 73564-69-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 7, p. 1879 - 1882

21
[ 15854-87-2 ]
[ 73564-69-9 ]

Reference： [1] Journal of the American Chemical Society, 2013, vol. 135, # 33, p. 12228 - 12240

22
[ 93-58-3 ]
[ 15854-87-2 ]
[ 126179-78-0 ]
[ 106047-17-0 ]
[ 106047-16-9 ]

Reference： [1] Tetrahedron Letters, 1989, vol. 30, # 26, p. 3433 - 3436

23
[ 76-09-5 ]
[ 15854-87-2 ]
[ 181219-01-2 ]

Reference： [1] Tetrahedron Letters, 2005, vol. 46, # 28, p. 4737 - 4740

24
[ 15854-87-2 ]
[ 87199-17-5 ]
[ 99163-12-9 ]

Reference： [1] Chemistry - An Asian Journal, 2018, vol. 13, # 9, p. 1108 - 1113

[ 15854-87-2 ] Synthesis Path-Downstream 1~88

1
[ 188290-36-0 ]
[ 15854-87-2 ]
[ 21298-54-4 ]
[ 21308-82-7 ]

Reference： [1]Heterocycles,1986,vol. 24,p. 799 - 803

2
[ 93-58-3 ]
[ 15854-87-2 ]
[ 126179-78-0 ]
[ 106047-17-0 ]
[ 106047-16-9 ]

Reference： [1]Tetrahedron Letters,1989,vol. 30,p. 3433 - 3436

3
[ 16494-36-3 ]
[ 15854-87-2 ]
[ 129770-70-3 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1990,vol. 63,p. 1968 - 1972

4
[ 15854-87-2 ]
[ 577-19-5 ]
[ 4282-49-9 ]

Reference： [1]Tetrahedron Letters,1993,vol. 34,p. 3421 - 3424

5
[ 15854-87-2 ]
[ 107-19-7 ]
[ 93524-95-9 ]

Yield	Reaction Conditions	Operation in experiment
78%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 20℃; for 3.0h;Inert atmosphere;	General procedure: 1-Propyn-1-ol (240 ol (240 μL, 4.06 mmol, 1.0 eq) was dropwised to a solution of 2-, or 3, or 4-iodopyridine (1.0 g, 4.88 mmol, 1.2 eq), CuI 38 mg, 0.204 m iodopyridine (1.0 g, 4.88 mmol, 1.2 eq), CuI (38 mg, 0.204 mmol, 5 mol%), and PdCl2(PPh3)2 (140 mg, 0.204 (140 mg, 0.204 μmol, 5 mol %) in Et 3N (27 mL). After stirring for 3 h N (27 mL). After stirring for 3 h N (27 mL). After stirring for 3 h N (27 mL). After stirring for 3 h N (27 mL). After stirring for 3 h N (27 mL). After stirring for 3 h N (27 mL). After stirring for 3 h at room temperature, the reacat room temperature, the reac at room temperature, the reac at room temperature, the reaction mixture was diluted wtih EtOAc (30 mL) and quenched with saturated NH4Cl solution (30 mL). The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuoin. Purification on silica gel column chromatography (hexane/EtOAc = 1:2) afforded 3-(2 ’-pyridinyl-2-propyn-1-ol (1a , 451451 mg, mg, 3.37 mmol, mol, 83 %) as a yellow powder.

Reference： [1]Journal of Photochemistry and Photobiology A: Chemistry,2011,vol. 222,p. 263 - 265
[2]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1984,vol. 33,p. 1433 - 1438
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1984,p. 1561 - 1566
[3]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 1031 - 1036
[4]Tetrahedron Letters,2017,vol. 58,p. 2856 - 2858
[5]Patent: WO2020/114487,2020,A1 .Location in patent: Paragraph 00392; 00446
[6]Heterocycles,2007,vol. 72,p. 665 - 671
[7]Patent: WO2020/114494,2020,A1 .Location in patent: Paragraph 00230; 00627
[8]Organic Letters,2020,vol. 22,p. 5423 - 5428

6
[ 15854-87-2 ]
[ 100-66-3 ]
[ 5938-16-9 ]
[ 4373-68-6 ]
[ 5958-00-9 ]

Reference： [1]Tetrahedron Letters,1989,vol. 30,p. 3433 - 3436

7
[ 15854-87-2 ]
[ 108-90-7 ]
[ 5957-96-0 ]
[ 4467-15-6 ]
[ 5957-92-6 ]

Reference： [1]Tetrahedron Letters,1989,vol. 30,p. 3433 - 3436

8
[ 15854-87-2 ]
[ 71-43-2 ]
[ 939-23-1 ]

Yield	Reaction Conditions	Operation in experiment
49%	With N,N'-diethylurea; potassium tert-butylate; at 110℃; for 24h;Schlenk technique; Sealed tube; Inert atmosphere;	General procedure: Aryl iodides (0.2 mmol) t-BuOK (0.6 mmol, 3.0 equiv), and U6 (0.02 mmol, 10 mol%) were added in dried Schlenk tubes. Benzene (2 mL) were added into tubes by syringe. The septum-sealed tube was evacuated and refilled with nitrogen three times. The mixture was stirred under a nitrogen atmosphere in sealed Schlenk tubes at 120 C for 24 h. The reaction was cooled down to room temperature. The mixture was filtered through a short plug of silica gel, washed with a copious amount of ethyl acetate. The combined organic phase was concentrated under vacuum. The product was purified through flash column chromatography on 300-400 mesh silica gel with hexane/ethyl acetate as eluent. Solvent was removed under vacuum to give the pure product.

Reference： [1]RSC Advances,2020,vol. 10,p. 14500 - 14509
[2]Journal of Organic Chemistry,2012,vol. 77,p. 7844 - 7849
[3]Catalysis Communications,2018,vol. 111,p. 95 - 99
[4]ACS Catalysis,2019,vol. 9,p. 6335 - 6341
[5]Heterocycles,1981,vol. 15,p. 1075 - 1078

9
[ 15854-87-2 ]
[ 201230-82-2 ]
[ 109-89-7 ]
[ 530-40-5 ]
N,N-diethyl α-oxo-4-pyridineacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine; tricyclohexylphosphine In dichloromethane at 50℃; for 6h;
90%	With tricyclohexylphosphine In dichloromethane at 50℃; for 6h;
1: 50 % Chromat. 2: 50 % Chromat.	With triethylamine In dichloromethane at 50℃; for 6h;

Reference： [1]Couve-Bonnaire, Samuel; Carpentier, Jean-Francois; Castanet, Yves; Mortreux, Andre [Tetrahedron Letters, 1999, vol. 40, # 19, p. 3717 - 3718]
[2]Couve-Bonnaire, Samuel; Carpentier, Jean-Francois; Mortreux, Andre; Castanet, Yves [Advanced Synthesis and Catalysis, 2001, vol. 343, # 3, p. 289 - 298]
[3]Couve-Bonnaire, Samuel; Carpentier, Jean-Francois; Castanet, Yves; Mortreux, Andre [Tetrahedron Letters, 1999, vol. 40, # 19, p. 3717 - 3718]

10
[ 15854-87-2 ]
[ 115378-31-9 ]
(R)-3-(tert-butoxycarbonyl)-4-[2-pyridin-4-ylethyl]-2,2-dimethyl-oxazolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	Stage #1: tert-butyl (4R)-2,2-dimethyl-4-vinyloxazolidine-3-carboxylate With 9-borabicyclo[3.3.1]nonane dimer In toluene at 80 - 85℃; Stage #2: 4-iodopyridine With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetra-(n-butyl)ammonium iodide In toluene at 90℃; Further stages.;

Reference： [1]Sabat, Mark; Johnson, Carl R. [Organic Letters, 2000, vol. 2, # 8, p. 1089 - 1091]

11
[ 15854-87-2 ]
[ 1066-54-2 ]
[ 133810-35-2 ]

Yield	Reaction Conditions	Operation in experiment
70.4%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; at 20℃; for 48h;Inert atmosphere;	To a solution of i1(5.Og, 24.39mmoi) and 2.64g, 26.Xmmoi) in lOOmL of Et3N was added Pd(lPh3)4 (1 .40g, I .22mmoi) and Cul (0.46g. 2.44inrnol). The reaction mixture was protected by N atmosphere, and was stirred at room temperature for 48 hours. TLC showed that the starting material was consumed, The reaction mixture was then concentrated in vacuo. Theresulting crude product was purified by silica gel column chromatography to give the target product 12(3. Og, yield 70.4%).
70.2%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; at 20℃; for 48h;Inert atmosphere;	To a solution of 5 (5Og, 24.39mrnoi) and 2 (2.64g, 26.8mrnol) in lOOmL of Et3N was added Pd(PPh3)4 (1 .40g, I 22mmol) and Cul (0.46g, 244mmoI). The reaction mixture was protected by N2 atmosphere, and was stirred at room temperature for 48 hours. TLC showed that the starting material was consumed. The reaction mixture was then concentrated in vacuo. The resulting crude product was purified by silica gel column chromatography to give the targetproduct 6 (3Og, yield: 702%).
	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;Inert atmosphere; Reflux;	The intermediates and final products were obtained via establishedcross-coupling reactions [5,15,17]. Briefly, 4-trimethylsililyethynylpyridine was obtained by reacting an equimolarquantity of 4-iodopyridine (2.0 mmol) with trimethylsilylethyne(TMSE, 2.0 mmol) in THF/iPrNH2 using Pd(II)/Cu(I) catalysts(Scheme 1). The crude product obtained was purified by silicacolumn chromatography using hexane/dichloromethane eluantsystems. This was followed by a protodesilylation reaction underbasic condition (aq. KOH in MeOH/THF) and the 4-ethynylpyridinewas separated by silica column chromatography using puredichloromethane as eluant. In the next phase of the reaction,respective aryl halides (2.0 mmol) and 4-ethynylpyridine (2.0mmol) were coupled via a Sonogashira cross-coupling reaction.Final products were purified using an alumina column and obtainedas tan to light brown solid in quantitative yields.

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 3057 - 3060
[2]Journal of the American Chemical Society,2013,vol. 135,p. 12228 - 12240
[3]Journal of the American Chemical Society,2017,vol. 139,p. 776 - 784
[4]Inorganic Chemistry,2018,vol. 57,p. 12113 - 12124
[5]Inorganic Chemistry,2015,vol. 54,p. 6055 - 6061
[6]Angewandte Chemie - International Edition,2019,vol. 58,p. 18424 - 18428
Angew. Chem.,2019,vol. 58,p. 18595 - 18599,5
[7]Crystal Growth and Design,2018,vol. 18,p. 6936 - 6945
[8]Chemical Communications,2018,vol. 54,p. 9305 - 9308
[9]Tetrahedron Letters,2010,vol. 51,p. 6839 - 6842
[10]Chemical Communications,2012,vol. 48,p. 8898 - 8900
[11]Patent: WO2017/117708,2017,A1 .Location in patent: Page/Page column 19
[12]Patent: WO2017/173604,2017,A1 .Location in patent: Page/Page column 18
[13]Beilstein Journal of Organic Chemistry,2011,vol. 7,p. 1499 - 1503
[14]MedChemComm,2019,vol. 10,p. 263 - 267
[15]Journal of Organometallic Chemistry,2019,vol. 892,p. 75 - 82

12
[ 15854-87-2 ]
[ 81290-20-2 ]
[ 3796-24-5 ]

Reference： [1]European Journal of Organic Chemistry,2002,p. 327 - 330
[2]Journal of the American Chemical Society,2008,vol. 130,p. 8600 - 8601

13
[ 15854-87-2 ]
[ 100-51-6 ]
[ 49826-70-2 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 4931 - 4935

14
[ 15854-87-2 ]
[ 640297-84-3 ]
3,8-bis[2-(4-pyridinyl)ethynyl]-1,10-phenanthroline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine In tetrahydrofuran at 60℃; for 6h;
85%	Stage #1: 4-iodopyridine; 3,8-bis(ethynyl)-1,10-phenanthroline With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ In tetrahydrofuran; triethylamine at 60℃; for 7h; Inert atmosphere; Stage #2: With potassium cyanide In methanol; dichloromethane; water for 1h; Inert atmosphere; Sonication;	General procedure: A flask was charged with 3,8-diethynylphenanthroline(229 mg, 1.0 mmol) and 3-iodopyridine(472 mg, 2.3 mmol), and dissolved with a solvent mixture of dry THF (90 ml) and triethylamine (9 ml). The Pd(PPh3)4 (116 mg, 0.10 mmol) and CuI (30 mg,0.16 mmol) were added to the flask. After the mixture was stirred at 60 C for 7 h, THF and triethylamine were removed by reduced pressure. The residue was dissolved with CH2Cl2-MeOH (95-5 ml) and added to an aqueous solution of KCN (1.0 g in 50 ml). After the solution was treated with ultrasonic irradiation for 1 h, the organic phase was separated and removed by rotary evaporation. The residue was further purified by SiO2 column chromatographywith CH2Cl2-MeOH (95:5-90:10, gradually) as eluent.
84%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 60℃; for 48h;

84%

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 60℃; for 48h;

Reference： [1]Resendiz, Marino J. E.; Noveron, Juan C.; Disteldorf, Hendrick; Fischer, Sonja; Stang, Peter J. [Organic Letters, 2004, vol. 6, # 5, p. 651 - 653]
[2]Shiotsuka, Michito; Ueno, Yusuke; Asano, Daiki; Matsuoka, Tomoya; Sako, Katsuya [Transition Metal Chemistry, 2015, vol. 40, # 6, p. 673 - 679]
[3]Ponce, Julia; Arroyo, Carlos R.; Tatay, Sergio; Frisenda, Riccardo; Gaviña, Pablo; Aravena, Daniel; Ruiz, Eliseo; Van Der Zant, Herre S. J.; Coronado, Eugenio [Journal of the American Chemical Society, 2014, vol. 136, # 23, p. 8314 - 8322]
[4]Ponce, Julia; Aragó, Juan; Vayá, Ignacio; Magenti, Jorge Gómez; Tatay, Sergio; Ortí, Enrique; Coronado, Eugenio [European Journal of Inorganic Chemistry, 2016, vol. 2016, # 12, p. 1851 - 1859]

15
[ 15854-87-2 ]
[ 3102-33-8 ]
(+/-)-4-(pyridin-4-yl)pentan-2-on [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With copper(l) iodide; n-butyllithium; Dibutyl sulfide In diethyl ether; hexane at 20℃; for 1h;

Reference： [1]Spivey, Alan C.; Shukla, Lena; Hayler, Judy F. [Organic Letters, 2007, vol. 9, # 5, p. 891 - 894]

16
[ 15854-87-2 ]
[ 6148-64-7 ]
[ 54401-85-3 ]

Yield	Reaction Conditions	Operation in experiment
82%	With magnesium chloride In ethanol Heating;

Reference： [1]Ho, Jonathan Z.; Braun, Matthew P. [Journal of labelled compounds and radiopharmaceuticals, 2007, vol. 50, # 5-6, p. 277 - 280]

17
[ 15854-87-2 ]
[ 189512-01-4 ]
C₁₆H₁₉N₃SO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate In N,N-dimethyl-formamide at 120℃; for 24h;

Reference： [1]Priego, Julián; Gutiérrez, Sonia; Ferritto, Rafael; Broughton, Howard B. [Synlett, 2007, # 19, p. 2957 - 2960]

18
[ 3581-89-3 ]
[ 15854-87-2 ]
[ 23899-30-1 ]

Reference： [1]Journal of Physical Organic Chemistry,2007,vol. 20,p. 894 - 899

19
[ 15854-87-2 ]
[ 581-47-5 ]

Reference： [1]Tetrahedron Letters,1987,vol. 28,p. 5845 - 5848

20
[ 15854-87-2 ]
[ 94839-07-3 ]
[ 339333-77-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; toluene; at 80℃; for 12h;	The mixture of 4-iodopyridine (400 mg, 1. 9 MMOL, 1 equiv), 1, 3-BENZODIOXOL-5-YL BORONIC ACID (323 mg, 1.9 mmol, 1 equiv), and PdCl2 (dppf) was dissolved in toluene/dioxane (5/1, 20 ML), and then 2 M sodium carbonate aq solution was added to the flask. The mixture was degassed and stirred at 80C for 12 h. The resulting mixture was filtered to remove solids, and the filtrate was washed by brine (10 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo. The resulting residue was separated by flash chromatography to yield desired product (350 mg, 90%).
48%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; toluene; at 80℃; for 6h;Inert atmosphere;	3,4-Methylene phenylboronic acid (146mg, 0.89mmol) and p-iodopyridine (180mg, 0.89mmol) are dissolved in 7.5mL toluene, 1.5mL 1,4 dioxane and 0.5mL water, add 18mg Pd (dppf)Cl2, sodium carbonate (137mg, 1.3mmol), under the protection of nitrogen, react at 80C for 6h, stop the reaction, filter to remove solids, wash with saturated brine, dry with anhydrous sodium sulfate, and separate on silica gel column, A brown solid (85 mg, 48%) was obtained.

Reference： [1]Patent: WO2004/58727,2004,A1 .Location in patent: Page 56
[2]Patent: CN111423454,2020,A .Location in patent: Paragraph 0163-0165; 0170-0171

21
[ 15854-87-2 ]
[ 34770-60-0 ]
[ 891790-20-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;copper(l) iodide; trans-1,2-cyclohexanediamine; In 1,4-dioxane; at 110℃;Heating in a sealed tube;	EXAMPLE 151 EPO <DP n="128"/>Preparation of 4-(4-methyl-2-piperazinon- 1 -yl)piperidin- 1 -yl-2-(2-methoxyphenyl)-2-(4- chlorophenylaminocarbonylamino)-acetamide; A. Preparation of 4-(4-methyl-2-piperazinon-l-yl)piperidine; [0523] To a solution of 2-pirhoerazinone (200 mg, 2.00 nimol) and HCHO (37% aq., 0.200 mL, 2.69 mmol) in MeOH (6 niL) at room temperature, NaBH3CN (162 mg, 2.57 mmol) was added. After being stirred at room temperature overnight, the solution was concentrated in vacuo. The residue was partitioned between 5% aq. NaHCO3 and nBuOH. The nBuOH phase was separated, concentrated in vacuo to give the <strong>[34770-60-0]4-methyl-2-piperazinone</strong> as a semi-solid (118 mg). MS 115.5 (M+H).[0524] A mixture of 4-iodopyridine (218 mg, 1.06 mmol), <strong>[34770-60-0]4-methyl-2-piperazinone</strong> (106 mg, 0.929 mmol), K3PO4 (425 mg, 2.00 mmol) and 1,2-trans-diaminocyclohexane (0.050 mL, 0.41 mmol) in anhydrous dioxane (3.0 mL) was degassed with Ar before being charged with CuI (40 mg, 0.21 mmol). The mixture in a sealed tube was heated at 1100C overnight. The mixture was purified by a prep-TLC using MeOHZCH2Cl2 (10/90) as solvents to give 1- (pyridin-4-yl)-<strong>[34770-60-0]4-methyl-2-piperazinone</strong> (42 mg). MS 192.5 (M+H).[0525] A mixture of l-(pyridin-4-yl)-<strong>[34770-60-0]4-methyl-2-piperazinone</strong> (12 mg, 0.063 mmol) and PtO2 (49 mg) in HOAc (6.0 mL) was hydrogenated on a Parr shaker under 40 psi for 3 days. The mixture was filtered through celite. The filtrate was concentrated in vacuo. The residue was dissolved in IN HCl (5.0 mL). The solution was then concentrated in vacuo to give the titled compound as hydrochloride salt (12 mg). MS 198.5 (M+H).

Reference： [1]Patent: WO2006/63113,2006,A2 .Location in patent: Page/Page column 126-127

22
[ 136466-94-9 ]
[ 15854-87-2 ]
[ 1000982-00-2 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 5175 - 5178

23
[ 15854-87-2 ]
[ 111-86-4 ]
[ 64690-19-3 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 6586 - 6596

24
[ 221675-35-0 ]
[ 15854-87-2 ]
[ 1041261-48-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; copper(l) iodide; trans-N,N'-dimethylcyclohexane-1,2-diamine; In toluene; at 130℃;Inert atmosphere;	Example 6; Compound 6N-(2-methylbenzothiazol-5-yl)-1-(4-pyridyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxamide6.1 ethyl 1-(4-pyridyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate0.2 g (1.05 mmol) of <strong>[221675-35-0]ethyl 1H-pyrrolo[2,3-b]pyridine-2-carboxylate</strong>, obtained according to the protocol described in step 3.2, 0.244 g (1.16 mmol) of 4-iodopyridine, 0.01 g (0.05 mmol) of copper iodide, 0.47 g (2.21 mmol) of tripotassium phosphate, 0.029 g (0.21 mmol) of racemic trans-N,N'-dimethylcyclohexane-1,2-diamine and 2 mL of toluene are introduced into a sealed 25 mL tube, equipped with a magnetic stirrer and maintained under an argon sparge. The reaction mixture is stirred under an argon sparge for 20 minutes and then rapidly sealed and maintained at 130 C. for 5 days. The cooled suspension is diluted in 10 mL of ethyl acetate and 20 mL of water. The aqueous phase is then extracted with twice 30 mL of ethyl acetate. The combined organic phases are successively washed with 10 mL of saturated aqueous sodium hydrogen carbonate solution, 10 mL of water and 10 mL of saturated aqueous sodium chloride solution. The resulting organic phase is then dried over sodium sulfate, filtered and concentrated under reduced pressure. 0.26 g of expected product is isolated in the form of a brown powder.1H NMR (DMSO D6), delta (ppm): 8.75 (d, 2H); 8.4 (m, 1H); 8.25 (m, 1H); 7.5 (m, 3H); 7.3 (m, 1H); 4.2 (q, 2H); 1.2 (t, 3H).

Reference： [1]Patent: US2009/298865,2009,A1 .Location in patent: Page/Page column 8-9

25
[ 53137-27-2 ]
[ 15854-87-2 ]
2,4-dimethyl-5-pyridinylthiazole [ No CAS ]

Reference： [1]Organic Letters,2010,vol. 12,p. 4745 - 4747

26
[ 15854-87-2 ]
[ 54001-16-0 ]
2-(4-methoxyphenyl)-4-methyl-5-pyridinylthiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With silver (II) carbonate; triphenylphosphine; palladium dichloride In N,N-dimethyl acetamide; toluene at 135℃; for 16h; Sealed tube;

Reference： [1]Zhang, Fengzhi; Greaney, Michael F. [Organic Letters, 2010, vol. 12, # 21, p. 4745 - 4747]

27
[ 15854-87-2 ]
[ 106833-79-8 ]
2-phenyl-5-pyridinyloxazole [ No CAS ]

Reference： [1]Organic Letters,2010,vol. 12,p. 4745 - 4747

28
[ 288-13-1 ]
[ 15854-87-2 ]
[ 25700-13-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	With copper(l) iodide; tetrabutylammomium bromide; N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine In water at 125℃; for 12h;	4.1 General procedure General procedure: Iodobenzene (1.0 mmol), imidazole (1.5 mmol), TEPA (2.0 mmol), TBAB (0.3 mmol), CuI (0.1 mmol), and 3 mL H2O were added to a 10 mL flask, which was subsequently capped with a rubber balloon. The mixture was stirred in a preheated oil bath at 125 °C for 12 h. After cooling the mixture to the room temperature, 5 mL water was added and the product was extracted by ethyl acetate (10 mL×3). The combined organic layer was washed by brine (15 mL), dried over anhydrous MgSO4, and evaporated under the reduced pressure. Further purification by silica gel column chromatography (6:1 petroleum ether/ethyl acetate) give the 1-phenyl-1H-imidazole.
86%	With copper(I) oxide; potassium phosphate monohydrate at 100℃; for 1h; Inert atmosphere; Microwave irradiation; sealed tube; Neat (no solvent);
83%	With copper(I) oxide; caesium carbonate In dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere;	4.2 General procedure for N-heteroarylation of nitrogen heterocycles General procedure: The N-nucleophile (0.735mmol), Cu2O (0.0735mmol), Cs2CO3 (1.47mmol), DMSO (0.3mL) and heteroaryl halide (1.103mmol) were added to a reaction vial and a screw cap was fitted to it. The reaction mixture was stirred under air in a closed system at 100°C for 24h. After cooling to room temperature, the mixture was diluted with dichloromethane and filtered through a pad of Celite. The combined organic extracts were dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by silica-gel column chromatography to afford the N-arylated product. The identity and purity of the products was confirmed by 1H, 13C NMR spectroscopic analysis and elemental analysis or mass spectroscopy.

Reference： [1]Yang, Qichao; Wang, Yufang; Yang, Li; Zhang, Mingjie [Tetrahedron, 2013, vol. 69, # 30, p. 6230 - 6233]
[2]Liu, Zhen-Jiang; Vors, Jean-Pierre; Gesing, Ernst R. F.; Bolm, Carsten [Green Chemistry, 2011, vol. 13, # 1, p. 42 - 45]
[3]Teo, Yong-Chua; Yong, Fui-Fong; Sim, Shirlyn [Tetrahedron, 2013, vol. 69, # 35, p. 7279 - 7284]

29
[ 15854-87-2 ]
[ 133810-44-3 ]
[ 1266361-93-6 ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 469 - 477

30
[ 15854-87-2 ]
trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt [ No CAS ]
[ 3796-24-5 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 1896 - 1900

31
[ 15854-87-2 ]
[ 123387-50-8 ]
cis-t-butyl 4-methyl-2-(pyridin-4-yl)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: 4-methylpiperidine-1-carboxylic acid tert-butyl ester With sec.-butyllithium; Trimethylenediamine In diethyl ether; hexane at -78℃; for 4h; Inert atmosphere; Stage #2: With zinc(II) chloride In tetrahydrofuran; diethyl ether; hexane at -78 - 20℃; for 0.25h; Inert atmosphere; Stage #3: 4-iodopyridine With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In tetrahydrofuran at 55℃; Inert atmosphere; optical yield given as %de; diastereoselective reaction;

Reference： [1]Seel, Stephanie; Thaler, Tobias; Takatsu, Keishi; Zhang, Cong; Zipse, Hendrik; Straub, Bernd F.; Mayer, Peter; Knochel, Paul [Journal of the American Chemical Society, 2011, vol. 133, # 13, p. 4774 - 4777]

32
[ 15854-87-2 ]
[ 2916-68-9 ]
[ 1338215-40-9 ]

Yield	Reaction Conditions	Operation in experiment
91%	With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In toluene at 110℃; for 14h; Inert atmosphere; Sealed tube;	General procedure for coupling reaction General procedure: An oven-dried resealable Schlenk tube were charged with CuI (10 mol %), 1,10-phenanthroline (20% mol), Cs2CO3 (1.4-2.0 mmol),aryl iodide (1.0 mmol).The Schlenk tube was evacuated and back-filled with argon and 2-trimethylsilyl alcohol (3mmol) and toluene (0.5 ml) were added. Schlenk tube was then sealed with a Teflon screw cap and placed in a preheated oil bath at 110°C for 14 h. The resulting suspension was cooled to room temperature and filtered through a 0.5 x 1 cm pad of silica gel, eluting with diethyl ether. The filtrate was concentrated. Purification of the residue by flash chromatography on silica gel gave the desired product.

Reference： [1]Dibakar, Mullick; Prakash, Anjanappa; Selvakumar, Kumaravel; Ruckmani, Kandasamy; Sivakumar, Manickam [Tetrahedron Letters, 2011, vol. 52, # 41, p. 5338 - 5341]

33
[ 15854-87-2 ]
[ 37968-97-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With copper(l) iodide; sodiumsulfide nonahydrate; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 18h; Inert atmosphere;
75%	With carbon disulfide; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 100℃; for 12h; Inert atmosphere; Sealed tube;
60%	With iron(II) chloride tetrahydrate; caesium carbonate; 2-sulfanyl-1,3-benzoxazole; copper(II) oxide In N,N-dimethyl-formamide at 135℃; for 24h; Inert atmosphere; Sealed tube;

Reference： [1]Location in patent: experimental part Li, Yaming; Nie, Caiping; Wang, Huifeng; Li, Xiaoying; Verpoort, Francis; Duan, Chunying [European Journal of Organic Chemistry, 2011, # 36, p. 7331 - 7338]
[2]Zhao, Peng; Yin, Hang; Gao, Hongxin; Xi, Chanjuan [Journal of Organic Chemistry, 2013, vol. 78, # 10, p. 5001 - 5006]
[3]Tber; Hiebel; El Hakmaoui; Akssira; Guillaumet; Berteina-Raboin [RSC Advances, 2016, vol. 6, # 76, p. 72030 - 72036]

34
[ 13436-48-1 ]
[ 15854-87-2 ]
[ 1429864-77-6 ]

Reference： [1]European Journal of Organic Chemistry,2012,p. 7075 - 7081

35
[ 15854-87-2 ]
[ 158525-01-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide; N-ethyl-N,N-diisopropylamine / water / 69.84 °C / Inert atmosphere; Darkness 2: sodium hydroxide / toluene / 4 h / 115.84 °C / Inert atmosphere 3: copper(I) bromide; triethylamine; bis-triphenylphosphine-palladium(II) chloride / 48 h / 59.84 - 89.84 °C / Inert atmosphere; Darkness

Reference： [1]Muñoz-Lara, Francisco J.; Gaspar, Ana B.; Muñoz, M. Carmen; Ksenofontov, Vadim; Real, José Antonio [Inorganic Chemistry, 2013, vol. 52, # 1, p. 3 - 5]

36
[ 15854-87-2 ]
[ 139042-59-4 ]
[ 1416907-83-9 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In tetrahydrofuran; hexane; at -70 - 20℃;	Intermediate 12.1 : 1-(6-Bromo-pyridin-3-yl)-1-pyridin-4-yl-ethanolA solution of 5-acetyl-2-bromopyridine (Aldrich) (1.2 g, 5.82 mmol) and 3-iodopyridine (EGA-Chemie) (1.193 g, 5.82 mmol) in THF (10ml) was immersed in a dry ice - acetone bath. n-BuLi (1.6M) in hexane (4.00 ml, 6.40 mmol) was added slowly by a syringe at - 70C (exothermic reaction.). The reaction was allowed to warm up slowly to room temperature and was stirred over night. The reaction mixture was cooled to-20C and quenched with H20 before dilution with ethyl acetate. The organic phase was separated and washed with brine. The organic phase was dried over Na2S04, filtered and concentrated in vacuo and dried to obtain title compound as off-white solid.HPLC: A = 0.44 min; F = 5.744 min; LC-MS: m/z 279.0 [M+H]+

Reference： [1]Patent: WO2012/175520,2012,A1 .Location in patent: Page/Page column 80-81

37
[ 15854-87-2 ]
[ 1251006-64-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: chloro-trimethyl-silane; ethylene dibromide; zinc / N,N-dimethyl acetamide / 1.5 h / 20 - 65 °C / Inert atmosphere 1.2: 2 h / 80 °C / Inert atmosphere 2.1: acetonitrile / 1 h / 80 °C / Inert atmosphere 3.1: sodium tetrahydroborate; sodium hydrogencarbonate / ethanol / 1.17 h / 0 - 20 °C / Inert atmosphere 4.1: hydrogen; palladium(II) hydroxide / ethanol / 96 h / 20 °C / 2585.81 Torr / Inert atmosphere
	Multi-step reaction with 4 steps 1: copper(l) iodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere 2: acetonitrile / 1 h / 80 °C 3: sodium tetrahydroborate; ethanol / 2 h / 0 °C 4: palladium 10% on activated carbon; palladium(II) hydroxide; hydrogen / ethanol; ethyl acetate / 18 h / 60 °C / 2585.81 Torr

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US2013/102584, 2013, A1
[2]Current Patent Assignee: ARVINAS - WO2021/194879, 2021, A1

38
[ 1453-58-3 ]
[ 15854-87-2 ]
[ 1138819-52-9 ]

Yield	Reaction Conditions	Operation in experiment
63%	With copper(I) oxide; caesium carbonate In dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere;	4.2 General procedure for N-heteroarylation of nitrogen heterocycles General procedure: The N-nucleophile (0.735mmol), Cu2O (0.0735mmol), Cs2CO3 (1.47mmol), DMSO (0.3mL) and heteroaryl halide (1.103mmol) were added to a reaction vial and a screw cap was fitted to it. The reaction mixture was stirred under air in a closed system at 100°C for 24h. After cooling to room temperature, the mixture was diluted with dichloromethane and filtered through a pad of Celite. The combined organic extracts were dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by silica-gel column chromatography to afford the N-arylated product. The identity and purity of the products was confirmed by 1H, 13C NMR spectroscopic analysis and elemental analysis or mass spectroscopy.

Reference： [1]Teo, Yong-Chua; Yong, Fui-Fong; Sim, Shirlyn [Tetrahedron, 2013, vol. 69, # 35, p. 7279 - 7284]

39
[ 271-63-6 ]
[ 15854-87-2 ]
[ 1448542-70-8 ]

Yield	Reaction Conditions	Operation in experiment
89%	With potassium phosphate In dimethyl sulfoxide at 80℃; for 5h; Inert atmosphere;	General procedure for Cu-NP catalyzed N-arylations of azoles with aryl halides General procedure: An oven dried two-necked round bottom flask was charged with aryl halide (1mmol) and K3PO4 (2mmol), evacuated, and backfilled with argon. The azole compound (1mmol) and 2mL of DMSO were added under argon. After that Cu-NP (1.6mmol) was added and the flask was again backfilled with argon. The flask was then immersed in a preheated oil bath at 80°C until the conversion was completed (detected by TLC). The cooled mixture was partitioned between ethyl acetate (10mL) and saturated NH4Cl (10mL). The aqueous layer was extracted with ethyl acetate (2×10mL), the organic layer was washed with brine (20mL), dried over anhydrous Na2SO4, and concentrated in vacuum. The residue was purified by column chromatography on silica gel using ethyl acetate in hexane (1.5-10%) as eluent to afford the desired product. All the products have been characterized by 1H NMR, 13C NMR, and mass spectroscopy. For new products, FTIR data were also recorded.Analytical data of compound 3a: 1H NMR (CDCl3, 500MHz): δ 7.94 (d, J=8.5Hz, 2H), 7.87 (d, J=8.5Hz, 2H), 7.78 (d, J=8.5Hz, 1H), 7.70-7.68 (m, 2H), 7.27-7.24 (m, 1H), 7.20-7.17 (m, 1H), 6.79 (d, J=3.5Hz, 1H); 13C NMR (CDCl3, 125MHz): δ 142.8, 135.5, 129.7, 128.3, 127.4, 126.9 (q, J=59Hz), 125.4 (q, J=362Hz), 123.9, 122.9, 121.4, 121.0, 110.3, 104.9; MS(EI) 262.4 (M+). Anal. Calcd for C15H10F3N: C, 68.96, H, 3.86, N, 5.36. Found: C, 68.89, H, 3.88, N, 5.33.
89%	With potassium phosphate; copper In dimethyl sulfoxide at 80℃; for 5h; Inert atmosphere;	General procedure for Cu-NP catalyzed N-arylations of azoles with aryl halides (Table 2): General procedure: An oven dried two-necked round bottom flask was charged with aryl halide (1mmol) and K3PO4 (2mmol), evacuated, and backfilled with argon. The azole compound (1mmol) and 2mL of DMSO were added under argon. After that Cu-NP (1.6mmol) was added and the flask was again backfilled with argon. The flask was then immersed in a preheated oil bath at 80°C until the conversion was completed (detected by TLC). The cooled mixture was partitioned between ethyl acetate (10mL) and saturated NH4Cl (10mL). The aqueous layer was extracted with ethyl acetate (2×10mL), the organic layer was washed with brine (20mL), dried over anhydrous Na2SO4, and concentrated in vacuum. The residue was purified by column chromatography on silica gel using ethyl acetate in hexane (1.5-10%) as eluent to afford the desired product. All the products have been characterized by 1H NMR, 13C NMR, and mass spectroscopy. For new products, FTIR data were also recorded.
82%	With copper(I) oxide; caesium carbonate In dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere;	4.2 General procedure for N-heteroarylation of nitrogen heterocycles General procedure: The N-nucleophile (0.735mmol), Cu2O (0.0735mmol), Cs2CO3 (1.47mmol), DMSO (0.3mL) and heteroaryl halide (1.103mmol) were added to a reaction vial and a screw cap was fitted to it. The reaction mixture was stirred under air in a closed system at 100°C for 24h. After cooling to room temperature, the mixture was diluted with dichloromethane and filtered through a pad of Celite. The combined organic extracts were dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by silica-gel column chromatography to afford the N-arylated product. The identity and purity of the products was confirmed by 1H, 13C NMR spectroscopic analysis and elemental analysis or mass spectroscopy.

Reference： [1]Pai, Gita; Chattopadhyay, Asoke P. [Tetrahedron Letters, 2014, vol. 55, # 4, p. 941 - 944]
[2]Pai, Gita; Chattopadhyay, Asoke P. [Tetrahedron Letters, 2014, vol. 55, # 4, p. 941 - 944]
[3]Teo, Yong-Chua; Yong, Fui-Fong; Sim, Shirlyn [Tetrahedron, 2013, vol. 69, # 35, p. 7279 - 7284]

40
[ 15854-87-2 ]
[ 133810-35-2 ]
[ 73564-69-9 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 12228 - 12240

41
[ 15854-87-2 ]
[ 18412-57-2 ]
[ 553-26-4 ]
[ 4423-10-3 ]

Yield	Reaction Conditions	Operation in experiment
40%	With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide at 120℃; for 12h; Inert atmosphere;

Reference： [1]Gurung, Santosh K.; Thapa, Surendra; Vangala, Adarsh S.; Giri, Ramesh [Organic Letters, 2013, vol. 15, # 20, p. 5378 - 5381]

42
[ 1826-13-7 ]
[ 15854-87-2 ]
[ 106950-02-1 ]

Reference： [1]Chemical Science,2013,vol. 5,p. 123 - 135

43
[ 3189-13-7 ]
[ 15854-87-2 ]
[ 1542750-01-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium phosphate; copper In dimethyl sulfoxide at 80℃; for 5h; Inert atmosphere;	General procedure for Cu-NP catalyzed N-arylations of azoles with aryl halides (Table 2): General procedure: An oven dried two-necked round bottom flask was charged with aryl halide (1mmol) and K3PO4 (2mmol), evacuated, and backfilled with argon. The azole compound (1mmol) and 2mL of DMSO were added under argon. After that Cu-NP (1.6mmol) was added and the flask was again backfilled with argon. The flask was then immersed in a preheated oil bath at 80°C until the conversion was completed (detected by TLC). The cooled mixture was partitioned between ethyl acetate (10mL) and saturated NH4Cl (10mL). The aqueous layer was extracted with ethyl acetate (2×10mL), the organic layer was washed with brine (20mL), dried over anhydrous Na2SO4, and concentrated in vacuum. The residue was purified by column chromatography on silica gel using ethyl acetate in hexane (1.5-10%) as eluent to afford the desired product. All the products have been characterized by 1H NMR, 13C NMR, and mass spectroscopy. For new products, FTIR data were also recorded.
	With potassium phosphate In dimethyl sulfoxide at 80℃; for 5h; Inert atmosphere;	General procedure for Cu-NP catalyzed N-arylations of azoles with aryl halides General procedure: An oven dried two-necked round bottom flask was charged with aryl halide (1mmol) and K3PO4 (2mmol), evacuated, and backfilled with argon. The azole compound (1mmol) and 2mL of DMSO were added under argon. After that Cu-NP (1.6mmol) was added and the flask was again backfilled with argon. The flask was then immersed in a preheated oil bath at 80°C until the conversion was completed (detected by TLC). The cooled mixture was partitioned between ethyl acetate (10mL) and saturated NH4Cl (10mL). The aqueous layer was extracted with ethyl acetate (2×10mL), the organic layer was washed with brine (20mL), dried over anhydrous Na2SO4, and concentrated in vacuum. The residue was purified by column chromatography on silica gel using ethyl acetate in hexane (1.5-10%) as eluent to afford the desired product. All the products have been characterized by 1H NMR, 13C NMR, and mass spectroscopy. For new products, FTIR data were also recorded.Analytical data of compound 3a: 1H NMR (CDCl3, 500MHz): δ 7.94 (d, J=8.5Hz, 2H), 7.87 (d, J=8.5Hz, 2H), 7.78 (d, J=8.5Hz, 1H), 7.70-7.68 (m, 2H), 7.27-7.24 (m, 1H), 7.20-7.17 (m, 1H), 6.79 (d, J=3.5Hz, 1H); 13C NMR (CDCl3, 125MHz): δ 142.8, 135.5, 129.7, 128.3, 127.4, 126.9 (q, J=59Hz), 125.4 (q, J=362Hz), 123.9, 122.9, 121.4, 121.0, 110.3, 104.9; MS(EI) 262.4 (M+). Anal. Calcd for C15H10F3N: C, 68.96, H, 3.86, N, 5.36. Found: C, 68.89, H, 3.88, N, 5.33.

44
[ 271-34-1 ]
[ 15854-87-2 ]
[ 1542750-10-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium phosphate; In dimethyl sulfoxide; at 80℃; for 5h;Inert atmosphere;	General procedure: An oven dried two-necked round bottom flask was charged with aryl halide (1mmol) and K3PO4 (2mmol), evacuated, and backfilled with argon. The azole compound (1mmol) and 2mL of DMSO were added under argon. After that Cu-NP (1.6mmol) was added and the flask was again backfilled with argon. The flask was then immersed in a preheated oil bath at 80C until the conversion was completed (detected by TLC). The cooled mixture was partitioned between ethyl acetate (10mL) and saturated NH4Cl (10mL). The aqueous layer was extracted with ethyl acetate (2×10mL), the organic layer was washed with brine (20mL), dried over anhydrous Na2SO4, and concentrated in vacuum. The residue was purified by column chromatography on silica gel using ethyl acetate in hexane (1.5-10%) as eluent to afford the desired product. All the products have been characterized by 1H NMR, 13C NMR, and mass spectroscopy. For new products, FTIR data were also recorded.Analytical data of compound 3a: 1H NMR (CDCl3, 500MHz): δ 7.94 (d, J=8.5Hz, 2H), 7.87 (d, J=8.5Hz, 2H), 7.78 (d, J=8.5Hz, 1H), 7.70-7.68 (m, 2H), 7.27-7.24 (m, 1H), 7.20-7.17 (m, 1H), 6.79 (d, J=3.5Hz, 1H); 13C NMR (CDCl3, 125MHz): δ 142.8, 135.5, 129.7, 128.3, 127.4, 126.9 (q, J=59Hz), 125.4 (q, J=362Hz), 123.9, 122.9, 121.4, 121.0, 110.3, 104.9; MS(EI) 262.4 (M+). Anal. Calcd for C15H10F3N: C, 68.96, H, 3.86, N, 5.36. Found: C, 68.89, H, 3.88, N, 5.33.
90%	With potassium phosphate; copper; In dimethyl sulfoxide; at 80℃; for 5h;Inert atmosphere;	General procedure: An oven dried two-necked round bottom flask was charged with aryl halide (1mmol) and K3PO4 (2mmol), evacuated, and backfilled with argon. The azole compound (1mmol) and 2mL of DMSO were added under argon. After that Cu-NP (1.6mmol) was added and the flask was again backfilled with argon. The flask was then immersed in a preheated oil bath at 80C until the conversion was completed (detected by TLC). The cooled mixture was partitioned between ethyl acetate (10mL) and saturated NH4Cl (10mL). The aqueous layer was extracted with ethyl acetate (2×10mL), the organic layer was washed with brine (20mL), dried over anhydrous Na2SO4, and concentrated in vacuum. The residue was purified by column chromatography on silica gel using ethyl acetate in hexane (1.5-10%) as eluent to afford the desired product. All the products have been characterized by 1H NMR, 13C NMR, and mass spectroscopy. For new products, FTIR data were also recorded.

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 941 - 944
[2]Tetrahedron Letters,2014,vol. 55,p. 941 - 944

45
[ 932378-94-4 ]
[ 15854-87-2 ]
[ 1262962-06-0 ]

Yield	Reaction Conditions	Operation in experiment
71.8%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; at 80℃; for 72h;Inert atmosphere;	4-iodopyridine (0.205 g, 1.0 mmol), benzene-1,3-dicarboxyethylester-5-boronic acid (0.64 g, 1.2 mmol), and K2CO3 (2.10 g,10.0 mmol) were added to 1,4-dioxane (30 mL). After stirring,Pd(PPh3)4 (0.05 g, 0.043 mmol) was added, then the mixture was heated to 80 C for 3 days under N2. The resultant was evaporated to dryness and taken up in CH2Cl2 which later had been dried overMgSO4. This CH2Cl2 solution was evaporated to dryness and theresidue was washed briefly with ethanol (20 mL). The crude productwas hydrolyzed by refluxing in 2 M aqueous NaOH followed byacidification with 37% HCl to afford H2L. Yield: 0.53 g, 71.8%. 1HNMR (DMSO-d6, 500 MHz), PIP: 8.7 (d, 2H), 8.54 (s, 1H) 8.48 (s,2H), 8.24 (d, 1H, J) 6.1 Hz), 7.81 (d, 2H). Anal. Calc. for H2L,C13H9O4N: C, 64.20; N, 5.76; H, 3.73. Found: C, 64.03; N, 5.68; H,3.79%.

Reference： [1]Inorganica Chimica Acta,2014,vol. 414,p. 141 - 144

46
[ 736990-02-6 ]
[ 15854-87-2 ]
[ 1349698-44-7 ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; water; at 50.0℃; for 24.0h;Reflux;	b) 5-Pyridin-4-yl-lH-indole-2-carboxylic acid ethyl ester Potassium acetate (2.57 g; 26.2 mmol) was dried under high vacuum at 50C in the reaction flask over 2 hours. 5-Bromo-lH-indole-2-carboxylic acid ethyl ester (2.34 g; 8.75 mmol) was dissolved in degassed dioxane (100 mL) and added to the reaction flask, followed by bis(pinacolato)diboron and bis(triphenylphosphine)palladium (II) chloride, (0.30 g; 0.44 mmol). The reaction mixture was heated to reflux under a nitrogen atmosphere and stirred for 17 hours. The reaction mixture was cooled to 50C. 4-Iodopyridine (3.58 g; 1.75 mmol) was added to the reaction portion wise, followed by bis(triphenylphosphine)palladium (II) chloride (0.30 g; 0.44 mmol) and 2 M aqueous sodium carbonate solution (23 mL). The reaction was returned to reflux and stirred for 24 hours. Following complete consumption of the intermediate, the reaction was cooled to room temperature and the solvent was removed in vacuo. The crude reaction mixture was re-dissolved in ethyl acetate (100 mL) and washed with water (50 mL) and brine (50 mL). The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo. Trituration with ethyl acetate / heptane afforded the title compound (1.35 g, 59 %). 1H NMR (400MHz, DMSO): delta (ppm) = 1.35 (3H, t, J = 7.09 Hz), 4.36 (2H, q, J = 7.09 MHz), 7.24 (1H, s), 7.58 (1H, d, J = 8.56 Hz), 7.70-7.73 (3H, m), 8.14 (1H, s), 8.60 (2H, d, J = 5.87 Hz), 12.08 (1H, s). HPLC-MS (purity); retention time = 89%; 1.28min. MS ISP (m/e): 267.2 (100) [(M+H)+].
1.35 g	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In water; at 50.0℃; for 24.0h;Reflux;	Potassium acetate (2.57 g; 26.2 mmol) was dried under high vacuum at 50C in the reaction flask over 2 hours. 5-Bromo-1H-indole-2-carboxylic acid ethyl ester (2.34 g; 8.75 mmol) was dissolved in degassed dioxane (100 mL) and added to the reaction flask, followed by bis(pinacolato)diboron and bis(triphenylphosphine)palladium (II) chloride, (0.30 g; 0.44 mmol). The reaction mixture was heated to reflux under a nitrogen atmosphere and stirred for 17 hours. The reaction mixture was cooled to 50C. 4-Iodopyridine (3.58 g; 1.75 mmol) was added to the reaction portion wise, followed by bis(triphenylphosphine)palladium (II) chloride (0.30 g; 0.44 mmol) and 2 M aqueous sodium carbonate solution (23 mL). The reaction was returned to reflux and stirred for 24 hours. Following complete consumption of the intermediate, the reaction was cooled to room temperature and the solvent was removed in vacuo. The crude reaction mixture was re-dissolved in ethyl acetate (100 mL) and washed with water (50 mL) and brine (50 mL). The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo. Trituration with ethyl acetate / heptane afforded the title compound (1.35 g, 59 %). 1H NMR (400MHz, DMSO): delta (ppm) = 1.35 (3H, t, J = 7.09 Hz), 4.36 (2H, q, J = 7.09 MHz), 7.24 (1H, s), 7.58 (1H, d, J= 8.56 Hz), 7.70-7.73 (3H, m), 8.14 (1H, s), 8.60 (2H, d, J= 5.87 Hz), 12.08 (1H, s). HPLC-MS (purity); retention time = 89%; 1.28min. MS ISP (m/e): 267.2 (100) [(M+H)+].

Reference： [1]Patent: WO2014/60386,2014,A1 .Location in patent: Page/Page column 44
[2]Patent: EP2722329,2014,A1 .Location in patent: Paragraph 0170

47
[ 15854-87-2 ]
potassium ferrocyanide [ No CAS ]
[ 100-48-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With mesoporous silica SBA-15 supported Cu₂O nanoparticles In N,N-dimethyl-formamide at 120℃; for 8h; Green chemistry;
92%	With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 12h;	General procedure for the cyanation of aryl halides General procedure: F mixture of aryl halide (1.0 mmol), K4Fe(CN)6 (0.17 mmol), K2CO3 (1.0 mmol) and Pd/CuO NPs(0.024 mol %) in DMF (5.0 mL) was heated at 120C for the appropriate time. After completion of the reaction, the mixture was cooled to room temperature and the catalyst separated from the reaction mixture using centrifuge. The resultant solution was extracted with Et2O (320 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure to give the crude product. The residue was purified by recrystallization using ethanol and water. The purity of the compounds was confirmed by 1H NMR.
90%	With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 15h; Schlenk technique; Green chemistry;

85%	With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 2h;	2.3. General procedure for cyanation reactions General procedure: A solution containing K4[Fe(CN)6] (0.17 mmol), aryl halide (1.0mmol), Na2CO3 (1.5 mmol), Fe3O4PMDP/Pd (45 mg, 1.5 mol%),and DMF (3 mL) was mixed under stirring at 120 °C for the specifiedtime. TLC was used to follow the reaction. At the end of thereaction, the obtained solution was cooled to ambient temperatureand filtered, and the residue was rinsed using ethyl acetate (3 10mL) to isolate the catalyst using a suitable magnet. Water phasecontaining ethyl acetate (30 mL) was mixed with the organic phaseto extreact the ethyl acetate from the water. The organic phase wasdried over Na2SO4. The products were resulted by evaporating theorganic solvent. If more purification was needed, the productswere passed through a short silica gel column using the eluent ofn-hexane. All the products are known substances and were comparedwith authentic specimens
85%	With sodium carbonate In N,N-dimethyl-formamide at 120℃;	2.2. General procedure for cyanation reactions catalyzed by Pd(at)CS-biguanidine General procedure: A solution containing K4[Fe(CN)6] (0.2 mmol), aryl halide (1.0 mmol), Na2CO3 (1.5 mmol), Pd(at)CS-biguanidine (50 mg,0.7 mol%), and DMF (3 ml) was mixed under stirring at 120 °C for the specified time. TLC was used to follow the reaction. At the end of the reaction, the obtained solution was cooled to ambient temperature and centrifuged, and the residue was rinsed using ethyl acetate (3 10 ml). Water phase containing ethyl acetate (30 mL) was mixed with the organic phase to extract the ethyl acetate from the water. The organic phase was dried over Na2SO4. The products were resulted by evaporating the organic solvent. If more purification was needed, the products were passed through a short silica gel column using the eluent of n-hexane. All the products are known substances and were compared with authentic specimens.
79%	With caesium carbonate In N,N-dimethyl-formamide at 130℃; for 10h; Schlenk technique;	Cyanation of aryl halides with K4Fe(CN)6; general procedure General procedure: A mixture of the aryl halide (1.0 mmol), K4Fe(CN)6 (0.22 mmol), Cs2CO3 (1.0 mmol), Pd-zeolite (0.025 mmol Pd) and 5 mL of solvent (DMF) was placed in a Schlenk tube (25 mL), and was vigorously stirred for 10 h at 130 °C. Upon completion, the mixture was cooled to room temperature, and diluted with ether and water. Organic layer was washed with brine, dried over MgSO4, filtered and evaporated under reduced pressure using rotary evaporator to give the crude product. The residue was purified by recrystallisation using ethanol and water. The purity of the compounds was checked by 1H NMR and yields are based on aryl halide. All the products are known and the spectroscopic data (FT-IR and NMR) and melting points were consistent with those reported in the literature.4-19,38,39
	With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 1h; Inert atmosphere; Green chemistry;	General procedure: A mixture of aryl halide (1.0 mmol), K4[Fe(CN)6](0.22 mmol), 0.05 g [PS-ttet-Pd(II)], and sodium carbonate(1.0 mmol) was stirred in 5 cm3 DMF at 120° C for 1 h under an argon atmosphere. To the aryl nitrile compound generated in situ was added sodium azide (1.5 mmol) and the mixture was stirred at 120° C for appropriate time. After completion of the reaction (as indicated by TLC), the catalyst was centrifuged, washed with EtOH and the residue was diluted with 35 cm3 ethyl acetate and 20 cm3 HCl(4 N) and stirred vigorously. The resultant organic layer was separated and the aqueous layer was extracted with 25 cm3 ethyl acetate. The combined organic layer was washed with 8 cm3 water and concentrated to give a crude product. Column chromatography using silica gel gave thepure product. All products were characterized by 1H NMR and melting point which were in agreement with literature
	With sodium carbonate In N,N-dimethyl-formamide at 120℃;

Reference： [1]Yin, Wenzhu; Liu, Rui; He, Guangke; Lv, Wangjie; Zhu, Hongjun [RSC Advances, 2014, vol. 4, # 71, p. 37773 - 37778]
[2]Nasrollahzadeh, Mahmoud [Tetrahedron Letters, 2016, vol. 57, # 3, p. 337 - 339]
[3]Nasrollahzadeh, Mahmoud; Jaleh, Babak; Fakhri, Parisa; Zahraei, Ali; Ghadery, Esmaeil [RSC Advances, 2015, vol. 5, # 4, p. 2785 - 2793]
[4]Veisi, Hojat; Hemmati, Saba; Safarimehr, Parisa [Journal of Catalysis, 2018, vol. 365, p. 204 - 212]
[5]Veisi, Hojat [Polyhedron, 2019, vol. 159, p. 212 - 216]
[6]Sajadi, S. Mohammad; Maham, Mehdi; Mahmoud, Sarbast Ahmad [Journal of Chemical Research, 2013, vol. 37, # 10, p. 620 - 622]
[7]Tajbakhsh, Mahmood; Alinezhad, Heshmatollah; Nasrollahzadeh, Mahmoud; Kamali, Taghi A. [Monatshefte fur Chemie, 2016, vol. 147, # 12, p. 2135 - 2142]
[8]Nasrollahzadeh, Mahmoud; Ghorbannezhad, Fatemeh; Sajadi, S. Mohammad [Applied Organometallic Chemistry, 2019, vol. 33, # 1]

48
[ 15854-87-2 ]
[ 5720-07-0 ]
[ 5938-16-9 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 3946 - 3954

49
[ 15854-87-2 ]
[ 2140-11-6 ]
[ 1616667-81-2 ]

Yield	Reaction Conditions	Operation in experiment
55%	With piperidine; copper(l) iodide; palladium diacetate; caesium carbonate; In N,N-dimethyl-formamide; at 120℃; for 1h;Microwave irradiation;	General procedure: To a microwave vial containing oven-dried 2',3'-O-isopropilideneinosine (1) (200 mg, 0.65 mmol) and Cs2CO3 (528 mg, 1.62 mmol), CuI (371 mg, 1.95 mmol), Pd(OAc)2 (7 mg, 0.03 mmol) and 4-iodoanisole (304 mg, 1.30 mmol) in dry DMF (5 mL) were added. The vial was sealed and deoxygenated. Then dried and deoxygenated piperidine (26 muL, 0.26 mmol) was added. The mixture was microwaved irradiated at 120 C for 1 h. The reaction mixture was diluted with 150 mL of dichloromethane:methanol (1:1) and filtered. The filtrate was evaporated to dryness and the residue obtained was purified by flash chromatography (dichloromethane:methanol, 10:1). The purified solid was solved in DMF, treated with Quadrasil MP overnight, filtered and coevaporated with diethyl ether to yield 140 mg (52%) of 2 as a white amorphous solid.

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 82,p. 459 - 465

50
[ 15854-87-2 ]
[ 2140-11-6 ]
[ 1616667-83-4 ]

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 82,p. 459 - 465

51
[ 31366-25-3 ]
[ 15854-87-2 ]
[ 1581771-50-7 ]

Yield	Reaction Conditions	Operation in experiment
71%	With palladium diacetate; caesium carbonate; tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane for 24h; Inert atmosphere; Reflux;

Reference： [1]Vajpayee, Vaishali; Bivaud, Sebastien; Goeb, Sebastien; Croue, Vincent; Allain, Magali; Popp, Brian V.; Garci, Amine; Therrien, Bruno; Salle, Marc [Organometallics, 2014, vol. 33, # 7, p. 1651 - 1658]

52
[ 15854-87-2 ]
[ 935-14-8 ]
[ 158525-01-0 ]

Yield	Reaction Conditions	Operation in experiment
88%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine In tetrahydrofuran at 55℃; Inert atmosphere;
75%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 50℃; Inert atmosphere;
25%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diisopropylamine In tetrahydrofuran; chloroform at 20℃; for 36h;

Reference： [1]Wang, Zhaoyang; Bai, Wei; Tong, Jiaqi; Wang, Yi Jia; Qin, Anjun; Sun, Jing Zhi; Tang, Ben Zhong [Chemical Communications, 2016, vol. 52, # 68, p. 10365 - 10368]
[2]Ozores, Haxel Lionel; Amorín, Manuel; Granja, Juan R. [Journal of the American Chemical Society, 2017, vol. 139, # 2, p. 776 - 784]
[3]Ji, Guipeng; Yang, Zhenzhen; Zhao, Yanfei; Zhang, Hongye; Yu, Bo; Xu, Jilei; Xu, Huanjun; Liu, Zhimin [Chemical Communications, 2015, vol. 51, # 34, p. 7352 - 7355]

53
[ 15854-87-2 ]
trimethylsilyl 2-chloro-2,2-difluoroacetate [ No CAS ]
[ 3796-24-5 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 2086 - 2089

54
[ 15854-87-2 ]
[ 219537-97-0 ]
[ 608528-49-0 ]

Yield	Reaction Conditions	Operation in experiment
50%	Stage #1: 1,2-bis(5-chloro-2-methylthien-3-yl)cyclopent-1-ene With n-butyllithium In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere; Schlenk technique; Stage #2: With boric acid tributyl ester In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Schlenk technique; Stage #3: 4-iodopyridine With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In tetrahydrofuran at 50℃; for 17h; Inert atmosphere; Schlenk technique;

Reference： [1]Hu, Fang; Jiang, Lina; Cao, Meijiao; Xu, Zhiqiang; Huang, Juanyun; Wu, Di; Yang, Wenchao; Liu, Sheng Hua; Yin, Jun [RSC Advances, 2015, vol. 5, # 8, p. 5982 - 5987]

55
[ 15854-87-2 ]
[ 108-27-0 ]
5-methyl-1-(pyridin-4-yl)pyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With copper(l) iodide; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; potassium carbonate In 1,4-dioxane at 150℃; Sealed tube; Inert atmosphere;	A mixture of 5-methylpyrrolidin-2-one (0.050 g, 0.50 mmcl), 4-iodopyridine (0.103 g, 0.50mmol), (trans)-N,N’-dimethylcyclohexane-1,2-diamine (0.016 mL, 0.10 mmcl), Cul (0.019 g,0.10 mmol) and K2C03 (0.209 g, 1.5 mmcl) in dioxane (2 mL) was sealed in a nitrogen flushedglass tube and heated with stirring at 150 °C overnight. The cooled reaction mixture wasconcentrated onto flash silica (5 mL). The resulting powder was purified by columnchromatography (normal phase, [Biotage SNAP cartridge KP-sil 25 g, 40-63 lm, 60 A], 30 mL per mm, 0 to 5% Solvent A in DCM, where Solvent A is 10% of (7 M NH3MeOH) in MeOH) to give 5-methyl-1-(pyridmn-4-yl)pyrrolidin-2-one (0.088 g, 99%) as an oil.LCMS (Method C): m/z 177 (M+H) (ES’), at 0.69 mm, UVactive

Reference： [1]Current Patent Assignee: SOSEI GROUP CORPORATION - WO2015/118342, 2015, A1 Location in patent: Page/Page column 102

56
[ 15854-87-2 ]
[ 17784-60-0 ]
4-(1-(pyridin-4-yl)-1H-pyrazol-3-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With copper(I) oxide; salicylaldehyde-oxime; caesium carbonate In N,N-dimethyl-formamide at 110℃; for 24h; Inert atmosphere;
	With potassium carbonate at 190℃; for 24h;

Reference： [1]Yokoyama, Hiroyuki; Ueda, Yoshihiro; Fujita, Daishi; Sato, Sota; Fujita, Makoto [Chemistry - An Asian Journal, 2015, vol. 10, # 10, p. 2292 - 2295]
[2]Li, Jun-Chi; Li, Hong-Xi; Li, Hai-Yan; Gong, Wei-Jie; Lang, Jian-Ping [Crystal Growth and Design, 2016, vol. 16, # 3, p. 1617 - 1625]

57
[ 274-56-6 ]
[ 15854-87-2 ]
[ 1383675-69-1 ]

Reference： [1]Organometallics,2016,vol. 35,p. 288 - 300

58
[ 15854-87-2 ]
[ 45887-08-9 ]
3-(1-(pyridin-4-yl)-1H-pyrazol-3-yl)pyridine [ No CAS ]

Reference： [1]Crystal Growth and Design,2016,vol. 16,p. 1617 - 1625

59
[ 1915-42-0 ]
[ 15854-87-2 ]
tri(pyridin-4-yl)amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With caesium carbonate; copper(I) bromide In 1-methyl-pyrrolidin-2-one at 190℃; for 8h; Inert atmosphere;

Reference： [1]Bureš, Filip; Cvejn, Daniel; Melánová, Klára; Beneš, Ludvík; Svoboda, Jan; Zima, Vítězslav; Pytela, Oldřich; Mikysek, Tomáš; Růžičková, Zdeňka; Kityk; Wojciechowski, Artur; Alzayed, Nasser [Journal of Materials Chemistry C, 2016, vol. 4, # 3, p. 468 - 478]

60
[ 268550-48-7 ]
[ 15854-87-2 ]
tert-butyl 1-oxo-2-(pyridin-4-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; copper(l) iodide; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; In toluene; at 110℃; for 24h;Sealed tube;	To a microwave vial was charged tert-butyl 1-oxo-2, 8-diazaspiro [4.5] decane-8-carboxylate (80 mg, 0.315 mmol) , 4-iodopyridine (64.5 mg, 0.315 mmol) , copper (I) iodide (3.00 mg, 0.016 mmol) , (1R, 2R) -N1, N2-dimethylcyclohexane-1, 2-diamine (9.92 muL, 0.063 mmol) , and potassium phosphate (134 mg, 0.629 mmol) . The vial was sealed, degased, and filled with toluene (1.6 mL) . The reaction mixture was heated at 110 for 24 h, diluted with water, and extracted with EtOAc. The organic layer was washed with brined, dried, evaporated to give the crude product, which was purified by silica gel column chromatography (0-10 MeOH/DCM) to give the title compound. LC/MS: (M+1) +: 332.05.

Reference： [1]Patent: WO2016/65582,2016,A1 .Location in patent: Page/Page column 58-59

61
[ 470-17-7 ]
[ 15854-87-2 ]
(4aS,8aR,9aS)-8a-methyl-5-methylidene-3-[(pyridin-4-yl)methyl]-4a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(4H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione; palladium diacetate; caesium carbonate; In N,N-dimethyl-formamide; at 0 - 120℃; for 16h;Inert atmosphere; Molecular sieve; Sealed tube;	General procedure: A glass ampoule was charged upon cooling to 0-5C under argon flow with 3A molecular sieves (10 mg), <strong>[470-17-7]isoalantolactone</strong> (1) (117 mg,0.5 mmol), halopyridine 2a-e (0.6 mmol), Pd(OAc)2(4.5 mg, 4 mol %), the appropriate ligand, base, and DMF(3 ml), as well as 1 equiv of TBAB when needed. The ampoule was sealed and heated for 16 h at 120. When the reaction was complete, the ampoule was cooled,opened, the mixture was filtered, the filtrate was poured into a saturated NaCl solution (30 ml) and extracted withEtOAc (3×30 ml). The combined organic extracts were washed with saturated NaCl solution (1×30 ml), water (2×30 ml), dried over MgSO4, and evaporated under reduced pressure provided by water aspirator. The oily residue was dissolved in a minimum amount of CHCl3 and separated by silica gel column chromatography (eluentCHCl3-EtOH, gradient 100:1?100:4). The starting lactone (1) was eluted first (in the case of incomplete conversion), followed by reaction products: compounds 3, then compounds 4, and homocoupling products: 3,3'-bipyridine,20 4,4'-bipyridine,21 3,3'-bis(5-methoxypyridine) (7).22

Reference： [1]Chemistry of Heterocyclic Compounds,2016,vol. 52,p. 165 - 171
Khim. Geterotsikl. Soedin.,2016,vol. 52,p. 165 - 171,7

62
[ 470-17-7 ]
[ 15854-87-2 ]
(4aS,8aR,9aS)-8a-methyl-5-methylidene-3-[(pyridin-4-yl)methyl]-4a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(4H)-one [ No CAS ]
(3aR,4aS,8aR,9aR,E)-8a-methyl-5-methylidene-3-[(pyridin-4-yl)methylidene]decahydronaphtho[2,3-b]furan-2(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%; 47%	With tetrabutylammomium bromide; palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; In N,N-dimethyl-formamide; at 0 - 120℃; for 16h;Inert atmosphere; Molecular sieve; Sealed tube;Catalytic behavior;	General procedure: A glass ampoule was charged upon cooling to 0-5C under argon flow with 3A molecular sieves (10 mg), <strong>[470-17-7]isoalantolactone</strong> (1) (117 mg,0.5 mmol), halopyridine 2a-e (0.6 mmol), Pd(OAc)2(4.5 mg, 4 mol %), the appropriate ligand, base, and DMF(3 ml), as well as 1 equiv of TBAB when needed. The ampoule was sealed and heated for 16 h at 120. When the reaction was complete, the ampoule was cooled,opened, the mixture was filtered, the filtrate was poured into a saturated NaCl solution (30 ml) and extracted withEtOAc (3×30 ml). The combined organic extracts were washed with saturated NaCl solution (1×30 ml), water (2×30 ml), dried over MgSO4, and evaporated under reduced pressure provided by water aspirator. The oily residue was dissolved in a minimum amount of CHCl3 and separated by silica gel column chromatography (eluentCHCl3-EtOH, gradient 100:1?100:4). The starting lactone (1) was eluted first (in the case of incomplete conversion), followed by reaction products: compounds 3, then compounds 4, and homocoupling products: 3,3'-bipyridine,20 4,4'-bipyridine,21 3,3'-bis(5-methoxypyridine) (7).22

Reference： [1]Chemistry of Heterocyclic Compounds,2016,vol. 52,p. 165 - 171
Khim. Geterotsikl. Soedin.,2016,vol. 52,p. 165 - 171,7

63
[ 15854-87-2 ]
[ 589-87-7 ]
[ 39795-60-3 ]

Yield	Reaction Conditions	Operation in experiment
102 g		4-iodoyridine 149g and THF 689mL flown into a flask, the temperature of the contents kept 1 °C, 2.0M isopropylmagnesium chloride THF soln. 400 ml is dropwise added. after dropwise addition 15 minutes stirred, tetramethylethylenediaminezinc(II) chloride complex 202g is added, with stirring, 25 minutes at room temperature. Next, p-bromoiodobenzene 226g and tetrakis(triphenylphosphine)palladium(0) 0.34g was added and heated to reflux for 3 hours. The reaction liquid cooling to room temperature, sodium salt aqueous acetic acid ethylenediaminediacetic 4 · 4 (730g/1.7L) is added, the organic layer. After intercalating organic layer is dried by a drying agent, distilling the crude product is obtained and the solvent is reduced. This crude product is silica gel column chromatography (developing solvent: toluene-toluene/ethyl acetate = 9/1 (volume ratio)) is purified by, 4-(4-bromophenyl)pyridine 102g is obtained.

Reference： [1]Patent: JP5907069,2016,B2 .Location in patent: Paragraph 0184

64
[ 470-17-7 ]
[ 15854-87-2 ]
[ 553-26-4 ]
(4aS,8aR,9aS)-8a-methyl-5-methylidene-3-[(pyridin-4-yl)methyl]-4a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(4H)-one [ No CAS ]
(3aR,4aS,8aR,9aR,E)-8a-methyl-5-methylidene-3-[(pyridin-4-yl)methylidene]decahydronaphtho[2,3-b]furan-2(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%; 29%	With palladium diacetate; caesium carbonate; tris-(o-tolyl)phosphine; In N,N-dimethyl-formamide; at 0 - 120℃; for 16h;Inert atmosphere; Molecular sieve; Sealed tube;	General procedure: A glass ampoule was charged upon cooling to 0-5C under argon flow with 3A molecular sieves (10 mg), <strong>[470-17-7]isoalantolactone</strong> (1) (117 mg,0.5 mmol), halopyridine 2a-e (0.6 mmol), Pd(OAc)2(4.5 mg, 4 mol %), the appropriate ligand, base, and DMF(3 ml), as well as 1 equiv of TBAB when needed. The ampoule was sealed and heated for 16 h at 120. When the reaction was complete, the ampoule was cooled,opened, the mixture was filtered, the filtrate was poured into a saturated NaCl solution (30 ml) and extracted withEtOAc (3×30 ml). The combined organic extracts were washed with saturated NaCl solution (1×30 ml), water (2×30 ml), dried over MgSO4, and evaporated under reduced pressure provided by water aspirator. The oily residue was dissolved in a minimum amount of CHCl3 and separated by silica gel column chromatography (eluentCHCl3-EtOH, gradient 100:1?100:4). The starting lactone (1) was eluted first (in the case of incomplete conversion), followed by reaction products: compounds 3, then compounds 4, and homocoupling products: 3,3'-bipyridine,20 4,4'-bipyridine,21 3,3'-bis(5-methoxypyridine) (7).22

Reference： [1]Chemistry of Heterocyclic Compounds,2016,vol. 52,p. 165 - 171
Khim. Geterotsikl. Soedin.,2016,vol. 52,p. 165 - 171,7

65
[ 15854-87-2 ]
[ 14389-12-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium carbonate / N,N-dimethyl-formamide / 1 h / 120 °C / Inert atmosphere; Green chemistry 2: sodium azide / N,N-dimethyl-formamide / 12 h / 120 °C / Inert atmosphere; Green chemistry
	Multi-step reaction with 2 steps 1: sodium carbonate; / N,N-dimethyl-formamide / 120 °C 2: ; sodium azide / N,N-dimethyl-formamide / 12 h / 120 °C

Reference： [1]Tajbakhsh, Mahmood; Alinezhad, Heshmatollah; Nasrollahzadeh, Mahmoud; Kamali, Taghi A. [Monatshefte fur Chemie, 2016, vol. 147, # 12, p. 2135 - 2142]
[2]Nasrollahzadeh, Mahmoud; Ghorbannezhad, Fatemeh; Sajadi, S. Mohammad [Applied Organometallic Chemistry, 2019, vol. 33, # 1]

66
[ 15854-87-2 ]
[ 940911-03-5 ]
5-(pyridin-4-ylethynyl)picolinaldehyde [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2016,vol. 11,p. 2662 - 2666

67
[ 15854-87-2 ]
[ 7037-49-2 ]

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 2856 - 2858

68
[ 15854-87-2 ]
[ 16282-16-9 ]
1,2-diphenyl-1-(pyridin-4-yl)butan-1-ol [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 6212 - 6215

69
[ 15854-87-2 ]
[ 57103-02-3 ]
4-(3,6-diiodo-9H-carbazol-9-yl)pyridine [ No CAS ]

Reference： [1]Chinese Journal of Chemistry,2017,vol. 35,p. 1869 - 1874

70
[ 15854-87-2 ]
[ 205877-26-5 ]
C₂₅H₁₈N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With piperidine; copper(l) iodide; In 1,4-dioxane; at 90℃; for 12h;Inert atmosphere;	General procedure: The appropriate mono-, di- or tri-acetylene TPA derivative(200 mg) and 4-iodopyridine were dissolved in a mixture ofdioxane/piperidine (25 mL, 4/1). Ar was bubbled through themixture for 10 min and [Pd(PPh3)4] and CuI were added. The reactionmixture was stirred at 90 C for 12 h. The cooled reactionmixture was diluted with H2O (50 mL) and extracted with CH2Cl2(2 50 mL). The combined organic extracts were thenwashed withsaturated NH4Cl solution, brine, and dried. Finally, the solventswere evaporated under vacuum and the crude productwas purifiedby column chromatography (SiO2, appropriate eluent). Chromophore 4. The title compound was synthesized from 4-ethynyltriphenylamine (200 mg, 0.743 mmol), 4-iodopyridine(167 mg, 0.817 mmol), [Pd(PPh3)4] (17.16 mg, 0.015 mmol) andCuI (2.83 mg, 0.015 mmol) following the general procedure forSonogashira cross-coupling. Yellow solid. Yield: 231 mg (90%). Rf:0.6 (SiO2, CHCl3/EtOAc 1/1). Mp: 196-197 C. 1H NMR (500 MHz,CDCl3): delta (ppm) 7.00 (d, 2H, 3J 8.5 Hz, CHAr), 7.08 (t, 2H, 3J 7.5 Hz,CHAr), 7.12 (d, 4H, 3J 7.5 Hz, CHAr), 7.28 (t, 4H, 3J 7.5 Hz, CHAr),7.33 (d, 2H, 3J 5.5 Hz, CHPy), 7.37 (d, 2H, 3J 8.5 Hz, CHAr), 8.56 (d,2H, 3J 5.5 Hz, CHPy). 13C NMR (125 MHz, CDCl3): delta (ppm) 86.2,94.9, 114.4, 121.8, 124.1, 125.4, 125.5, 129.7, 132.0, 133.1, 147.1, 148.9,149.9. HR-MALDI-MS (DHB): calcd for C25H18N2 (M) 346.1465,found 346.1473.

Reference： [1]Dyes and Pigments,2017,vol. 146,p. 467 - 478

71
[ 15854-87-2 ]
[ 189178-09-4 ]
[ 359647-66-8 ]

Yield	Reaction Conditions	Operation in experiment
85%		General procedure: The appropriate mono-, di- or tri-acetylene TPA derivative(200 mg) and 4-iodopyridine were dissolved in a mixture ofdioxane/piperidine (25 mL, 4/1). Ar was bubbled through themixture for 10 min and [Pd(PPh3)4] and CuI were added. The reactionmixture was stirred at 90 C for 12 h. The cooled reactionmixture was diluted with H2O (50 mL) and extracted with CH2Cl2(2 50 mL). The combined organic extracts were thenwashed withsaturated NH4Cl solution, brine, and dried. Finally, the solventswere evaporated under vacuum and the crude productwas purifiedby column chromatography (SiO2, appropriate eluent).

Reference： [1]Dyes and Pigments,2017,vol. 146,p. 467 - 478

72
[ 15854-87-2 ]
[ 1240785-42-5 ]
(Z)-1,2-diphenyl-1,2-bis(4-(pyridin-4-ylethynyl)-phenyl)-ethene [ No CAS ]
(E)-1,2-diphenyl-1,2-bis(4-(pyridin-4-ylethynyl)-phenyl)-ethene [ No CAS ]

Reference： [1]Journal of Physical Chemistry B,2018,vol. 122,p. 2165 - 2176

73
[ 15854-87-2 ]
[ 1692-15-5 ]
[ 553-26-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	With palladium diacetate; potassium carbonate In toluene at 80℃;	5 Example 5 4-Iodopyridine: 4-pyridine boronic acid: palladium acetate: potassium carbonate = 1:1.5:0.01:1.5, solvent is toluene, solvent The amount was 5 times that of 4-iodopyridine and the reaction temperature was 80°C.In other operations such as Example 1, the product yield was 86%, the purity was 99%
	With sodium carbonate; potassium carbonate In toluene at 80℃; for 6h; Inert atmosphere;	6 General procedure: Under nitrogen protection, 4-pyridyl trifluoromethanesulfonate:4-pyridineboronic acid:bistriphenylphosphine palladium dichloride:potassium carbonate=1:1.5:0.01:1.5 was added to toluene in a molar ratio. Toluene is 5-fold times the volumetric multiple of 4-pyridyloxytrifluoromethanesulfonate, and the reaction temperature is 80°C. After 6 hours, the reaction is completed, cooled to room temperature, and filtered.Wash the filter cake with 2 volumes (based on 4-pyridyl trifluoromethanesulfonate) in toluene and collect the mother liquor.The mother liquor was washed sequentially with 3 times 2% sodium hydroxide solution (based on 4-pyridyl trifluoromethanesulfonate) and the mother liquor was washed twice with water (based on 4-pyridyl trifluoromethanesulfonate) three times.Then, the methyl chloride was passed into the organic phase under stirring, solids were precipitated, stirred at room temperature for 1 hour, filtered, and the filter cake was collected to obtain a white solid, paraquat, with a yield of 88%, a purity of 99%,

Reference： [1]Current Patent Assignee: SHANDONG RAINBOW INVESTMENT CO., LTD. - CN107698494, 2018, A Location in patent: Paragraph 0049; 0050; 0051; 0052; 0053; 0054; 0058-0063
[2]Current Patent Assignee: SHANDONG RAINBOW INVESTMENT CO., LTD. - CN107935918, 2018, A Location in patent: Paragraph 0053-0058; 0062-0067

74
[ 15854-87-2 ]
[ 87199-17-5 ]
[ 99163-12-9 ]

Reference： [1]Chemistry - An Asian Journal,2018,vol. 13,p. 1108 - 1113

75
[ 15854-87-2 ]
[ 104-94-9 ]
[ 35488-09-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium phosphate; tris(1,10-phenanthroline)ruthenium(II) complex; [Ni(2,2′:6′,2''-terpyridine)(pyridine)(CH₃CN)₂](PF₆)₂ In acetonitrile for 24h; Irradiation;

Reference： [1]Key, Ryan J.; Vannucci, Aaron K. [Organometallics, 2018, vol. 37, # 9, p. 1468 - 1472]

76
[ 15854-87-2 ]
[ 107-18-6 ]
[ 2629-72-3 ]
[ 13603-28-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetramethylammonium formiate; triphenylphosphine In water; N,N-dimethyl-formamide at 80℃; for 16h; Overall yield = 36 %; regioselective reaction;

Reference： [1]Gurak, John A.; Engle, Keary M. [ACS Catalysis, 2018, vol. 8, # 10, p. 8987 - 8992]

77
[ 15854-87-2 ]
[ 645-66-9 ]
[ 1816-00-8 ]

Yield	Reaction Conditions	Operation in experiment
53%	With pyridine N-oxide; [2,2]bipyridinyl; potassium fluoride; lithium chloride; nickel dichloride; zinc In N,N-dimethyl acetamide at 0 - 25℃; for 24h;

Reference： [1]Chen, Hui; Hu, Lu; Ji, Wenzhi; Yao, Licheng; Liao, Xuebin [ACS Catalysis, 2018, vol. 8, # 11, p. 10479 - 10485]

78
[ 15854-87-2 ]
[ 3034-38-6 ]
4-(4-nitro-1H-imidazol-1-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8%	With copper(l) iodide; potassium carbonate; L-proline; at 95℃; for 48h;	A mixture of 4-iodopyridine (421a) (7.6 g, 37.1 mmol), L-proline (1.71 g, 14.83 mmol), copper(I) iodide (1.412 g, 7.41 mmol), 4-nitro-lH-imidazole (8.38 g, 74.1 mmol) and K2C03(10.25 g, 74.1 mmol) was degassed by vacuum /Ar-filled method (2chi). Into the degassed mixture DMSO (10 mL) was added. The reaction mixture was again degassed, sealed and heated at 95C for 2 days, cooled to room temperature, diluted with water. The resulting mixture was extracted with dichloromethane (2x). The combined extracts were washed with water, dried, filtered and concentrated under reduced pressure. The residue was purified by chromatography [silica (24 g), eluting with EtOAc in hexane from 0-100%] to give 4-(4- nitro-lH-imidazol-l-yl)pyridine (421b) (550 mg, 8% yield) as a yellow solid;1H MR (300 MHz, DMSO-i) delta 9.23 (d, J = 1.6 Hz, 1H), 8.79 (d, J = 1.6 Hz, 1H), 8.77 (d, J = 1.6 Hz, 1H), 8.74 (d, J = 1.6 Hz, 1H), 7.95 (d, J = 1.7 Hz, 1H), 7.94 (d, J = 1.7 Hz, 1H); MS (ES+): 191.1 (M+l).

Reference： [1]Patent: WO2018/232094,2018,A1 .Location in patent: Page/Page column 523; 524

79
[ 15854-87-2 ]
[ 110210-11-2 ]
[ 2767-90-0 ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 5003 - 5007
Angew. Chem.,2019,vol. 131,p. 5057 - 5061,5

80
[ 15854-87-2 ]
[ 175345-90-1 ]
4-((4-((triisopropylsilyl)ethynyl)phenyl)ethynyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine In chloroform at 40℃;

Reference： [1]Langenstroer, Anja; Kartha, Kalathil K.; Dorca, Yeray; Droste, Jörn; Stepanenko, Vladimir; Albuquerque, Rodrigo Q.; Hansen, Michael Ryan; Sánchez, Luis; Fernández, Gustavo [Journal of the American Chemical Society, 2019, vol. 141, # 13, p. 5192 - 5200]

81
[ 15854-87-2 ]
[ 195602-17-6 ]
4-(2,2',3,3'-tetrahydro-[5,5'-bithieno[3,4-b][1,4]dioxin]-7-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	With potassium acetate; palladium diacetate; In N,N-dimethyl-formamide; at 80℃;Inert atmosphere;	4-lodopyridine (0.1 09 g, 0.531 mmol) was dissolved in anhydrous DMF (7 ml) before 2,23,3'-tetrahydro-5,5'-bithieno[3,4-b][1 ,4]dioxine (0.2 g, 0.708 mmol), potassium acetate (0.209 g, 2.125 mmol) and Pd(OAc)2 (0.012 g, 0.053 mmol) were added and the reaction heated to 80 C under nitrogen overnight. After cooling to room temperature, the reaction mixture was poured into water (50 ml), stirred for 20 mins then filtered and washed with water (2 chi 50 ml). The residual solids were digested with ethyl acetate (3 chi 50 ml), combined, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Purification was achieved using column chromatography (ethyl acetate) to give 4-(2,2',3,3'-tetrahydro-[5,5'-bithieno[3,4-b][1 ,4]dioxin]-7-yl)pyridine (94 mg, 37%) as a yellow solid (mp. 190 C, dec). 1 H NMR (CDCI3, 400 MHz) delta 8.52 (2H, d, J = 6.4 Hz, ArH), 7.60 (2H, d, J = 6.4 Hz, ArH), 6.36 (1 H, s, ArH), 4.42-4.39 (6H, m, CH2), 4.29-4.27 (2H, m, CH2); 13C NMR (CDCI3, 100 MHz) delta 149.9, 141 .3, 140.7, 140.4, 137.9, 1 37.3, 128.5, 1 19.4, 1 1 1 .5, 1 1 1 .3, 109.4, 99.0, 65.2, 64.9, 64.7, 64.6; LRMS (El, m/z) 359.3.

Reference： [1]Patent: WO2018/37230,2018,A1 .Location in patent: Page/Page column 17; 18

82
[ 15854-87-2 ]
[ 376584-76-8 ]
[ 133617-47-7 ]

Yield	Reaction Conditions	Operation in experiment
78%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; Aliquat 336; methyl-tri-(decyl)-ammonium chloride In water; toluene at 150℃; for 0.166667h; Inert atmosphere; Microwave irradiation; Sealed tube;

Reference： [1]Ruiz-Carretero, Amparo; Atoini, Youssef; Han, Tianyan; Operamolla, Alessandra; Ippolito, Stefano; Valentini, Cataldo; Carrara, Serena; Sinn, Stephan; Prasetyanto, Eko Adi; Heiser, Thomas; Samorì, Paolo; Farinola, Gianluca; De Cola, Luisa [Journal of Materials Chemistry A, 2019, vol. 7, # 28, p. 16777 - 16784]

83
[ 15854-87-2 ]
[ 104987-11-3 ]
C₄₉H₇₂N₂O₁₂ [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2019,vol. 10,p. 1279 - 1283

84
[ 637-69-4 ]
[ 7031-93-8 ]
[ 15854-87-2 ]
C₂₃H₃₂N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With 2,6-di(t-butyl)-4-phenylphenol; caesium carbonate In dimethyl sulfoxide at 20℃; for 16h; Irradiation; Inert atmosphere;

Reference： [1]Li, Xipan; Liang, Kangjiang; Liu, Qian; Shen, Lei; Wei, Delian; Xia, Chengfeng; Zheng, Liyan [Chemical Science, 2020, vol. 11, # 27, p. 6996 - 7002]

85
[ 5117-12-4 ]
[ 15854-87-2 ]
1-morpholino-2-(pyridin-4-yl)propan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetramethylammonium formiate; P(p-C₆H₄F)3 In 1,4-dioxane; water at 80℃; for 4h; Sealed tube;

Reference： [1]Cherney, Emily C.; Engle, Keary M.; Gurak, John A.; Joe, Candice L.; Vasquez, Alena M. [Journal of the American Chemical Society, 2020, vol. 142, # 23, p. 10477 - 10484]

86
zinc(II)-bis(5,15-(2,4,6-trimethylphenyl))porphyrin [ No CAS ]
[ 64443-05-6 ]
[ 15854-87-2 ]
[ 25677-69-4 ]
[ 183294-82-8 ]
C₃₈H₃₂N₄Zn*C₅H₄IN [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane-d2 at 24.84℃;

Reference： [1]Paul, Indrajit; Rajasekaran, Vishnu Verman; Schmittel, Michael [Chemical Communications, 2020, vol. 56, # 84, p. 12821 - 12824]

87
[ 15854-87-2 ]
[ 1168135-03-2 ]
5-(4-pyridyl)-2,1,3-benzothiadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate In 1,4-dioxane; water at 120℃; for 0.5h; Inert atmosphere; Microwave irradiation;	6 Example 6: Preparation of 5-(4-pyridyl)-2,1 ,3-benzothiadiazole A microwave vial was charged, under nitrogen atmosphere, with 4-iodopyridine (0.1 g), 5-(4, 4,5,5- tetramethyl-1 ,3, 2-dioxaborolan-2-yl)-2,1 ,3-benzothiadiazole (0.141 g), 1 ,1'- bis(diphenylphosphino)ferrocene-palladium(ll)dichloride dichloromethane complex (0.04 g), cesium carbonate (0.239 g), 1 ,4-dioxane (0.805 mL) and water (0.268 mL). The mixture was heated at 120°C under microwave irradiation for 30 minutes. The reaction mixture was diluted with dichloromethane, filtered through a pad of celite, which was washed with further dichloromethane. The filtrate was concentrated and purified by silica gel chromatography eluting with a mixture of ethyl acetate and hexanes to give 5-(4-pyridyl)-2,1 ,3-benzothiadiazole as an off-white solid. 1H NMR (400 MHz, CDCl3) 8.77 (br s, 2H), 8.28 (dd, 1 H), 8.14 (dd, 1 H), 7.89 (dd, 1 H), 7.63 (d, 2H)

Reference： [1]Current Patent Assignee: SINOCHEM HOLDINGS CORPORATION LTD; Syngenta (in: Sinochem Holdings) - WO2021/58595, 2021, A1 Location in patent: Page/Page column 78

88
[ 3634-89-7 ]
[ 15854-87-2 ]
[ 101938-75-4 ]

Yield	Reaction Conditions	Operation in experiment
76.5%	Stage #1: p-iodopyridine With isopropylmagnesium chloride lithium chloride complex; copper chloride (I) In tetrahydrofuran; toluene at 0℃; for 0.0333333h; Inert atmosphere; Sealed tube; Stage #2: N-(p-toluenesulfonyl)aziridine In tetrahydrofuran; toluene at 0 - 55℃; for 18h; Inert atmosphere; Sealed tube; regioselective reaction;

Reference： [1]Han, Zhengxu S.; Jang, Hwanjong; Jiang, Qi; Ju, Xuan; Kim, Wan Shin; Lee, Jaehee; Lee, Miseon; Payne, Jenna; Wang, Xiao-Jun; Williams, Suja; Wu, Linglin; Zeng, Xingzhong [Organic Letters, 2022, vol. 24, # 14, p. 2655 - 2659]

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P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 15854-87-2 ] {[proInfo.proName]}

Quality Control of [ 15854-87-2 ]

Related Doc. of [ 15854-87-2 ]

Product Details of [ 15854-87-2 ]

Calculated chemistry of [ 15854-87-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 15854-87-2 ]

Application In Synthesis of [ 15854-87-2 ]

[ 15854-87-2 ] Synthesis Path-Upstream 1~24

[ 15854-87-2 ] Synthesis Path-Downstream 1~88

Related Parent Nucleus of [ 15854-87-2 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Parent Nucleus of
[ 15854-87-2 ]