[ CAS No. 1120-90-7 ] {[proInfo.proName]}

Name: 1120-90-7|3-Iodopyridine|98%
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SKU: A176020
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Quality Control of [ 1120-90-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1120-90-7 ]

SDS Specification

Alternatived Products of [ 1120-90-7 ]

Product Details of [ 1120-90-7 ]

CAS No. :	1120-90-7	MDL No. :	MFCD00023553
Formula :	C₅H₄IN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XDELKSRGBLWMBA-UHFFFAOYSA-N
M.W :	205.00	Pubchem ID :	70714
Synonyms :

Calculated chemistry of [ 1120-90-7 ]

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) :	-6.27 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.58
Log Po/w (XLOGP3) :	1.8
Log Po/w (WLOGP) :	1.69
Log Po/w (MLOGP) :	1.41
Log Po/w (SILICOS-IT) :	2.47
Consensus Log Po/w :	1.79

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.88
Solubility :	0.271 mg/ml ; 0.00132 mol/l
Class :	Soluble
Log S (Ali) :	-1.69
Solubility :	4.19 mg/ml ; 0.0204 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 :	1.97

Safety of [ 1120-90-7 ]

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

Application In Synthesis of [ 1120-90-7 ]

* 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 [ 1120-90-7 ]
Downstream synthetic route of [ 1120-90-7 ]

[ 1120-90-7 ] Synthesis Path-Upstream 1~42

1
[ 626-55-1 ]
[ 1120-90-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With copper(l) iodide; sodium iodide; N,N`-dimethylethylenediamine In 1,4-dioxane at 110℃; for 18 h; Inert atmosphere; Schlenk technique	Aromatic Finkelstein Reaction; General ProcedureThe reaction was carried out under argon using standard Schlenktechniques due to the moisture and oxygen sensitivity of the copper(I) iodide. A two-neck pear-shaped flask equipped with a refluxcondenser was charged with the (het)aryl bromide starting material,NaI (2 equiv per bromine to exchange), and CuI (5 molpercent per bromineto exchange). N,N′-Dimethylethylenediamine (L1) or N,N′-dimethyl-1,2-cyclohexanediamine (L2) (10 molpercent per bromine toexchange) and anhydrous 1,4-dioxane (0.5 mL per 1 mmol NaI)were added. The resulting suspension was heated to 110 °C for 18h. After cooling to r.t., the mixture was poured into aq 25percent NH3 solution.The blue solution was diluted to a doubled volume with H2Oand was extracted three times with CH2Cl2. In the case of the 2,2′-bipyridines, the combined organic phases were additionally washedwith aq EDTA solution. Otherwise, the combined organic phaseswere solely washed with brine and dried with MgSO4. The solventwas removed under reduced pressure to give the desired product inpure form. If needed, the crude product can be purified by columnchromatography or recrystallization.

Reference： [1] Synthesis (Germany), 2014, vol. 46, # 8, p. 1085 - 1090
[2] Tetrahedron Letters, 1999, vol. 40, # 23, p. 4339 - 4342
[3] Tetrahedron, 2000, vol. 56, # 10, p. 1349 - 1360
[4] Chemistry - A European Journal, 2010, vol. 16, # 41, p. 12425 - 12433
[5] Chemical & Pharmaceutical Bulletin, 1982, vol. 30, # 5, p. 1731 - 1737

2
[ 1692-25-7 ]
[ 1120-90-7 ]

Yield	Reaction Conditions	Operation in experiment
53%	With 1,10-Phenanthroline; oxygen; potassium iodide; copper(ll) bromide In N,N-dimethyl-formamide at 80℃; for 20 h;	General procedure: under oxygen, a sealed reaction tube was charged with KX (X = I, Br) (0.2 mmol), arylboronic acid (0.3 mmol), CuBr₂ (4.5 mg, 10 mol percent), 1,10-phen (7.2 mg, 20 mol percent) and DMF (2 mL). The mixture was stirred at 80 or 130 °C. After the completion of the reaction, the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel to give the product.

Reference： [1] Tetrahedron Letters, 2011, vol. 52, # 16, p. 1993 - 1995

3
[ 462-08-8 ]
[ 1120-90-7 ]

Reference： [1] Synthesis, 2007, # 1, p. 81 - 84
[2] RSC Advances, 2017, vol. 7, # 86, p. 54881 - 54891
[3] Tetrahedron Letters, 1998, vol. 39, # 25, p. 4533 - 4536
[4] Synthesis, 2009, # 6, p. 941 - 944
[5] Phosphorus and Sulfur and the Related Elements, 1984, vol. 21, p. 197 - 204
[6] Journal of Organic Chemistry, 2014, vol. 79, # 12, p. 5586 - 5594
[7] Justus Liebigs Annalen der Chemie, 1931, vol. 486, p. 95[8] Chem. Zentralbl., 1929, vol. 100, # II, p. 489
[9] Journal of the Chemical Society, 1953, p. 3226,3229
[10] Chemistry - A European Journal, 2016, vol. 22, # 48, p. 17407 - 17415

4
[ 22447-55-8 ]
[ 1120-90-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With phosphorus trichloride In dichloromethane for 1 h; Reflux	General procedure: A solution of iodopyridine 1-oxide 2a, 3a, or 7a (2 mmol) in CH₂Cl₂ (20 mL) was added dropwise to PCl₃ (0.5 mL) at 0 °C. The resulting solution was refluxed for 1 h, poured onto ice (10 g), and basified with aq 10 N NaOH (100 mL). The aqueous phase was extracted with CH₂Cl₂ (3 * 10 mL), the combined organic extracts were dried(Na₂SO₄), filtered, and concentrated.

Reference： [1] Synthesis (Germany), 2018, vol. 50, # 6, p. 1368 - 1372

5
[ 59-67-6 ]
[ 1120-90-7 ]

Yield	Reaction Conditions	Operation in experiment
65%	With N-iodo-succinimide; [4,4’-bis(tert-butyl)-2,2’-bipyridine]bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl]phenyl]iridium(III) hexafluorophosphate; iodine; caesium carbonate In acetonitrile at 50℃; for 24 h; Inert atmosphere; Irradiation; Sealed tube	General procedure: To a 15 mL test tube with septum Cs2CO3 (0.6 mmol, 195 mg), aromaticcarboxylic acid (1) (0.3 mmol), [Ir(dF(CF3)ppy)2dtbbpy]PF6 (D) (6 μmmol, 6.7 mg), NIS (1.5mmol, 337.5 mg) and I2 (60 μmol, 20 molpercent) were added. The tube was evacuated and backfilledwith argon for three times, and then 3 mL of dry CH3CN was added through a syringer underargon. The tube was sealed with Parafilm M® and placed in an oil bath with a contact thermometer,and the reaction was carried out at 50 °C under irradiation with 6 × 5 W blue LEDs (λmax = 455nm). After 24 h, the resulting mixture was filtered through a 2 cm thick pad of silica, and the silicawas washed with DCM) (50 mL). The filtrate was collected and the solvent was removed in vacuo.The crude residue was purified by silica gel flash column chromatography to provide the targetproduct (2). (Note: The reaction was very sensitive to moisture, and the yields sharply decreased to less than 5percent when 0.01 equivalent of H2O was added to the reaction system).

Reference： [1] Synlett, 2018, vol. 29, # 12, p. 1572 - 1577
[2] Journal of Organic Chemistry, 1983, vol. 48, # 19, p. 3297 - 3301
[3] Journal of Organic Chemistry, 1983, vol. 48, # 19, p. 3297 - 3301
[4] Heterocycles, 1981, vol. 16, # 1, p. 132

6
[ 5428-90-0 ]
[ 1120-90-7 ]

Reference： [1] Heterocycles, 1981, vol. 16, # 1, p. 132
[2] Journal of Organic Chemistry, 1983, vol. 48, # 19, p. 3297 - 3301

7
[ 20738-78-7 ]
[ 1120-90-7 ]

Reference： [1] Journal of Organic Chemistry, 1983, vol. 48, # 19, p. 3297 - 3301

8
[ 41408-73-5 ]
[ 1120-90-7 ]

Reference： [1] Journal of Organic Chemistry, 1983, vol. 48, # 19, p. 3297 - 3301
[2] Heterocycles, 1981, vol. 16, # 1, p. 132

9
[ 20260-53-1 ]
[ 1120-90-7 ]

Reference： [1] Nature Chemistry, 2018, vol. 10, # 10, p. 1016 - 1022

10
[ 59020-09-6 ]
[ 1120-90-7 ]

Reference： [1] Heterocycles, 1981, vol. 16, # 7, p. 1161 - 1164

11
[ 626-55-1 ]
[ 110-86-1 ]
[ 1120-90-7 ]

Reference： [1] Synthesis, 2009, # 22, p. 3823 - 3827

12
[ 1310816-15-9 ]
[ 630-19-3 ]
[ 1120-90-7 ]
[ 1210053-16-9 ]

Reference： [1] Heterocycles, 2011, vol. 83, # 4, p. 837 - 847

13
[ 1310816-15-9 ]
[ 1120-90-7 ]
[ 791-28-6 ]

Reference： [1] Heterocycles, 2009, vol. 78, # 11, p. 2735 - 2739

14
[ 110-86-1 ]
[ 1120-90-7 ]
[ 53710-18-2 ]

Reference： [1] Chemische Berichte, 1937, vol. 70, p. 1159,1160

15
[ 116195-81-4 ]
[ 1120-90-7 ]
[ 1210053-16-9 ]

Reference： [1] Heterocycles, 2011, vol. 83, # 4, p. 837 - 847

16
[ 110-86-1 ]
[ 7664-93-9 ]
[ 7446-11-9 ]
[ 7553-56-2 ]
[ 1120-90-7 ]
[ 53710-18-2 ]

Reference： [1] Chemische Berichte, 1937, vol. 70, p. 1159,1160

17
[ 631-61-8 ]
[ 1120-90-7 ]

Reference： [1] Chemische Berichte, 1925, vol. 58, p. 2021

18
[ 1120-90-7 ]
[ 6443-85-2 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 6, p. 1513 - 1517

19
[ 1120-90-7 ]
[ 67-63-0 ]
[ 88111-63-1 ]

Reference： [1] Organic letters, 2002, vol. 4, # 6, p. 973 - 976
[2] RSC Advances, 2016, vol. 6, # 88, p. 85186 - 85193

20
[ 1120-90-7 ]
[ 66-71-7 ]
[ 67-63-0 ]
[ 88111-63-1 ]

Reference： [1] Patent: US2003/65187, 2003, A1,

21
[ 1120-90-7 ]
[ 26260-02-6 ]
[ 176690-44-1 ]

Reference： [1] Synlett, 2005, # 2, p. 267 - 270

22
[ 1120-90-7 ]
[ 108-95-2 ]
[ 2176-45-6 ]

Reference： [1] Journal of Catalysis, 2017, vol. 348, p. 146 - 150
[2] Catalysis Science and Technology, 2013, vol. 3, # 8, p. 2025 - 2031
[3] Synlett, 2012, # 1, p. 101 - 106

23
[ 1120-90-7 ]
[ 100-67-4 ]
[ 2176-45-6 ]

Reference： [1] Journal of the American Chemical Society, 1937, vol. 59, p. 297,299

24
[ 1120-90-7 ]
[ 2176-45-6 ]

Reference： [1] ChemistryOpen, 2014, vol. 3, # 1, p. 19 - 22
[2] ChemistryOpen, 2014, vol. 3, # 1, p. 19 - 22

25
[ 1120-90-7 ]
[ 6148-64-7 ]
[ 39931-77-6 ]

Reference： [1] Journal of Labelled Compounds and Radiopharmaceuticals, 2007, vol. 50, # 5-6, p. 277 - 280

26
[ 1120-90-7 ]
[ 141-97-9 ]
[ 39931-77-6 ]

Reference： [1] Chemical Communications, 2013, vol. 49, # 60, p. 6767 - 6769

27
[ 1120-90-7 ]
[ 137344-20-8 ]
[ 39931-77-6 ]

Reference： [1] Journal of Labelled Compounds and Radiopharmaceuticals, 2007, vol. 50, # 5-6, p. 277 - 280

28
[ 1120-90-7 ]
[ 5764-82-9 ]
[ 39931-77-6 ]

Reference： [1] Chemical & Pharmaceutical Bulletin, 1985, vol. 33, # 10, p. 4309 - 4313
[2] Journal of Labelled Compounds and Radiopharmaceuticals, 2007, vol. 50, # 5-6, p. 277 - 280

29
[ 1120-90-7 ]
[ 3250-74-6 ]

Reference： [1] Monatshefte fur Chemie, 2016, vol. 147, # 12, p. 2135 - 2142

30
[ 1120-90-7 ]
[ 2567-81-9 ]
[ 6938-06-3 ]

Yield	Reaction Conditions	Operation in experiment
54%	With palladium diacetate In 1-methyl-pyrrolidin-2-one at 20 - 140℃; for 24 h; Inert atmosphere	General procedure: An oven-dried Schlenk-tube (10 mL) was charged with Pd source (1 mol percent), and ethyl potassium oxalate (0.75 mmol). The tube was evacuated and backfilled with argon (this procedure was repeated three times). After that, iodobenzene (0.5 mmol) and NMP (1.0 mL) were added by syringe under a counter flow of argon at room temperature. The reaction vessel was closed and then placed under stirring in a preheated oil bath. The reaction mixture was stirred for 24 h. Upon completion of the reaction, the mixture was cooled to room temperature and diluted with ethyl acetate, and analyzed by gas chromatography.

Reference： [1] Tetrahedron Letters, 2012, vol. 53, # 43, p. 5796 - 5799

31
[ 1120-90-7 ]
[ 13675-18-8 ]
[ 1692-25-7 ]

Reference： [1] Chemical Science, 2016, vol. 7, # 6, p. 3676 - 3680

32
[ 1120-90-7 ]
[ 471-25-0 ]
[ 59608-01-4 ]

Reference： [1] Journal of Organic Chemistry, 2011, vol. 76, # 7, p. 2214 - 2219

33
[ 288-13-1 ]
[ 1120-90-7 ]
[ 25700-11-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	With copper(l) iodide; manganese(II) fluoride; (1R,2R)-1,2-diaminocyclohexane; potassium hydroxide In water at 100℃; for 48 h;	General procedure: The N-nucleophile (1.47 mmol), CuI (Sigma-Aldrich, 99.999percent purity, 0.147 mmol), MnF2 (Sigma-Aldrich, 98percent purity, 0.441 mmol), KOH (2.94 mmol), the aryl halide (2.21 mmol), trans-1,2-diaminocyclohexane (0.294 mmol) and water (0.75 mL) 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 60C for 24 h. After cooling to room temperature, the mixture was diluted with dichloromethane and filtered through a pad of Celite. The combined organic extracts were dried with 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 known products was confirmed by 1H and 13C NMR spectroscopic analysis.

Reference： [1] Tetrahedron Letters, 2011, vol. 52, # 52, p. 7171 - 7174

34
[ 288-13-1 ]
[ 1120-90-7 ]
[ 25700-12-3 ]

Yield	Reaction Conditions	Operation in experiment
83%	With copper(I) oxide; caesium carbonate In dimethyl sulfoxide at 100℃; for 24 h; Inert atmosphere	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] Tetrahedron Letters, 2009, vol. 50, # 42, p. 5868 - 5871
[2] Green Chemistry, 2011, vol. 13, # 1, p. 42 - 45
[3] Tetrahedron, 2013, vol. 69, # 35, p. 7279 - 7284

35
[ 288-13-1 ]
[ 1120-90-7 ]
[ 25700-12-3 ]
[ 25700-13-4 ]

Reference： [1] Journal of Organic Chemistry, 2011, vol. 76, # 2, p. 654 - 660

36
[ 1120-90-7 ]
[ 60753-14-2 ]

Reference： [1] Patent: WO2014/144836, 2014, A2,

37
[ 1120-90-7 ]
[ 651358-83-7 ]
[ 106047-28-3 ]

Reference： [1] Organic Letters, 2009, vol. 11, # 2, p. 381 - 384

38
[ 1120-90-7 ]
[ 73183-34-3 ]
[ 329214-79-1 ]

Reference： [1] Journal of the American Chemical Society, 2017, vol. 139, # 2, p. 607 - 610

39
[ 1120-90-7 ]
[ 78782-17-9 ]
[ 329214-79-1 ]

Reference： [1] Journal of the American Chemical Society, 2017, vol. 139, # 2, p. 975 - 984

40
[ 1120-90-7 ]
[ 87199-17-5 ]
[ 127406-55-7 ]

Reference： [1] Advanced Synthesis and Catalysis, 2011, vol. 353, # 11-12, p. 1889 - 1896

41
[ 1120-90-7 ]
[ 1122-91-4 ]
[ 127406-55-7 ]

Reference： [1] Tetrahedron Letters, 2004, vol. 45, # 20, p. 3909 - 3912

42
[ 1120-90-7 ]
[ 939430-30-5 ]

Reference： [1] Patent: WO2012/140243, 2012, A1,

[ 1120-90-7 ] Synthesis Path-Downstream 1~88

1
[ 110-86-1 ]
[ 1120-90-7 ]
[ 53710-18-2 ]

Reference： [1]Chemische Berichte,1937,vol. 70,p. 1159,1160

2
[ 1120-90-7 ]
[ 100-67-4 ]
[ 2176-45-6 ]

Reference： [1]Journal of the American Chemical Society,1937,vol. 59,p. 297,299

3
[ 109-04-6 ]
[ 1120-90-7 ]
[ 581-50-0 ]

Reference： [1]Tetrahedron Letters,1992,vol. 33,p. 5373 - 5374
[2]Tetrahedron,1993,vol. 49,p. 9713 - 9720

4
[ 1120-90-7 ]
[ 56475-87-7 ]
[ 13078-04-1 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 2464 - 2470

5
[ 1120-90-7 ]
[ 1001-26-9 ]
(Z)-3-Ethoxy-3-pyridin-3-yl-acrylic acid ethyl ester [ No CAS ]

Reference： [1]Heterocycles,1988,vol. 27,p. 257 - 260

6
[ 1120-90-7 ]
[ 6414-69-3 ]
[ 64107-54-6 ]

Reference： [1]Synthesis,1988,p. 485 - 486

7
[ 1120-90-7 ]
[ 7425-53-8 ]
[ 60753-13-1 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 9756 - 9766
[2]Synthesis,1988,p. 485 - 486

8
[ 1120-90-7 ]
[ 17997-47-6 ]
[ 581-50-0 ]

Reference： [1]Journal of Organometallic Chemistry,1993,vol. 460,p. 127 - 130

9
[ 1120-90-7 ]
[ 100-66-3 ]
[ 4373-67-5 ]
[ 5958-01-0 ]
[ 5958-02-1 ]

Reference： [1]Tetrahedron Letters,1989,vol. 30,p. 3433 - 3436
[2]Heterocycles,1981,vol. 15,p. 1075 - 1078

10
[ 110-86-1 ]
[ 7664-93-9 ]
[ 7446-11-9 ]
[ 7553-56-2 ]
[ 1120-90-7 ]
[ 53710-18-2 ]

Reference： [1]Chemische Berichte,1937,vol. 70,p. 1159,1160

11
disodium-salt of/the/ <5-hydroxy-penta-2,4-dienyliden>-amidosulfuric acid [ No CAS ]
[ 1120-90-7 ]
[ 53710-18-2 ]

Reference： [1]Chemische Berichte,1939,vol. 72,p. 859

12
[ 1120-90-7 ]
[ 81290-20-2 ]
[ 3796-23-4 ]

Reference： [1]European Journal of Organic Chemistry,2002,p. 327 - 330
[2]Journal of the American Chemical Society,2008,vol. 130,p. 8600 - 8601
[3]Organic Letters,2014,vol. 16,p. 4268 - 4271

13
[ 1120-90-7 ]
[ 1885-38-7 ]
[ 76132-45-1 ]
(E)-3-phenyl-3-(pyridin-3-yl)-2-propenenitrile [ No CAS ]

Reference： [1]Synthesis,2002,p. 1903 - 1911

14
[ 1120-90-7 ]
[ 501435-91-2 ]
5-bromo-2-fluoro-[3,3']bipyridyl [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 3352 - 3355

15
[ 1120-90-7 ]
[ 1122-91-4 ]
[ 127406-55-7 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 3909 - 3912

16
[ 123-75-1 ]
[ 1120-90-7 ]
[ 110-86-1 ]
[ 532-12-7 ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 13244 - 13246

17
[ 1120-90-7 ]
[ 927-74-2 ]
[ 138487-20-4 ]

Yield	Reaction Conditions	Operation in experiment
78%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; for 16.0h;Reflux; Inert atmosphere; Schlenk technique;	3-Iodopyridine (16b, 500 mg, 2.44 mmol, 1 eq) was dissolved under N2 atmosphere in triethylamine (20 mL). CuI (13.9 mg, 0.08 mmol, 0.03 eq), Pd(PPh3)4 (56.4 mg, 0.05 mmol, 0.02 eq) and but-3-yn-1-ol (7, 0.27 mL, 3.61 mmol, 1.48 eq) were added and the solution was heated to reflux for 16 h. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography (d = 3 cm, h = 15 cm, V = 20 mL, cyclohexane:ethyl acetate = 4:1 ethyl acetate). Orange oil, yield 279 mg (1.90 mmol, 78 %). C9H9NO (147.2). Rf = 0.28 (ethyl acetate). HPLC: 92.8 %, tR = 3.49 min. 1H NMR (400 MHz, CDCl3): delta [ppm] = 2.52 (s, 1H, OH), 2.71 (t, J = 6.3 Hz, 2H, PyCCCH2CH2OH), 3.84 (t, J = 6.3 Hz, 2H, PyCCCH2CH2OH), 7.22 (ddd, J = 8.1/4.9/0.9 Hz, 1H, 5-Hpyridine), 7.69 (dt, J = 7.9/1.9 Hz, 1H, 4-Hpyridine), 8.49 (dd, J = 5.0/1.7 Hz, 1H, 6-Hpyridine), 8.61 - 8.66 (m, 1H, 2-Hpyridine). 13C NMR (101 MHz, CDCl3): delta [ppm] = 24.0 (1C, PyCCCH2CH2OH), 61.0 (1C, PyCCCH2CH2OH), 79.0 (1C, PyCCCH2CH2OH), 90.8 (1C, PyCCCH2CH2OH), 120.9 (1C, C-3pyridine), 123.2 (1C, C-5pyridine), 139.0 (1C, C-4pyridine), 148.1 (1C, C-6pyridine), 152.3 (1C, C-2pyridine). IR: v[cm-1] = 3271 (O-H), 2936, 2878 (C-Haliph.), 2236 (C? C), 1563, 1477 (C=Carom.), 1408 (CH2 deform.), 1045 (C-OH). Exact Mass (APCI): m/z = 148.0756 (calcd. 148.0757 for C9H10NO [MH]+).
77%	With sodium phosphate dodecahydrate; palladium 10% on activated carbon; In water; isopropyl alcohol; at 80.0℃; for 0.5h;	In a degassed 20 mL vial, commercially available 3-iodopyridine (0.5 g, 2.44 mmol), 3-butyn-1-ol (0.22 mL, 2.93 mmol), 10% Pd/C (0.01 g, 0.01 mmol) and sodium phosphate tribasicdodecahydrate (1.85 g, 4.88 mmol) were dissolved in a 1:1 mixture of i-PrOH/H20 (10 mL). The suspension was vigorously stirred and heated at 80 C for 30 mm. The crude mixture was diluted with EtOAc (40 mL) and H20 (40 mL), filtered and separated. The corresponding aqueous layer was washed with EtOAc (4 x 25 mL), and the collected organic layer was dried over Na2504,filtered and concentrated to dryness giving an oily residue (0. 56 g). Purification by typical silicagel flash chromatography (Cy/EtOAc, 25:75) afforded the pure title compound (0.331 g, 77%),as an oil. R= 1.22 mm. MS (ESI) m/z: 148 [M-H]. ?H NMR (DMSO-d6): oe 8.59-8.57 (m, 1H),8.51 (dd, 1H, J= 4.8, 1.7 Hz), 7.80 (dt, 1H, J= 7.9, 1.7 Hz), 7.38 (ddd, 1H, J= 7.9, 4.8, 0.7 Hz),4.92 (t, 1H, J= 5.8 Hz), 3.60 (q, 2H, J= 5.8 Hz), 2.59 (t, 2H, J= 6.7 Hz).

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 1717 - 1720
[2]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 3559 - 3567
[3]Patent: WO2014/144836,2014,A2 .Location in patent: Paragraph 0612; 0613
[4]Chemistry - A European Journal,2008,vol. 14,p. 6994 - 6999

18
[ 1120-90-7 ]
[ 80673-00-3 ]
[ 50559-45-0 ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 2697 - 2703

19
[ 1120-90-7 ]
[ 71460-02-1 ]
[ 848132-24-1 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 1791 - 1795

20
[ 1120-90-7 ]
[ 26260-02-6 ]
[ 176690-44-1 ]

Reference： [1]Synlett,2005,p. 267 - 270

21
[ 1120-90-7 ]
[ 107263-89-8 ]
3-[(E)-2-(2-Methyl-thiazol-4-yl)-vinyl]-pyridine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1080 - 1100

22
[ 1120-90-7 ]
[ 171596-36-4 ]
(6R,12aR)-6-Benzo[1,3]dioxol-5-yl-2-pyridin-3-yl-2,3,6,7,12,12a-hexahydro-pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione [ No CAS ]
(6R,12aS)-6-benzo[1,3]dioxol-5-yl-2-pyridin-3-yl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 789 - 792

23
[ 5029-67-4 ]
[ 1120-90-7 ]
[ 581-50-0 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 3589 - 3591

24
[ 1120-90-7 ]
[ 6148-64-7 ]
[ 39931-77-6 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2007,vol. 50,p. 277 - 280

25
[ 1120-90-7 ]
[ 251453-07-3 ]
[ 5958-02-1 ]

Reference： [1]Organic Letters,1999,vol. 1,p. 1495 - 1498

26
[ 3581-89-3 ]
[ 1120-90-7 ]
5-methyl-2-(3'-pyridyl)thiazole [ No CAS ]

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

27
[ 1120-90-7 ]
[ 581-50-0 ]

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

28
[ 1120-90-7 ]
[ 766-83-6 ]
[ 866684-52-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In ethyl acetate; at 20℃; for 18.0h;	Add triethylamine (0. 55 mL, 3. 92 mmol), copper (I) iodide (19 mg, 0. 098 mmol) and bis (triphenylphosphine) palladium (II) dichloride (35 mg, 0. 049 mmol) to a solution of 3-iodopyridine (200 mg, 0. 97 mmol) and 1-chloro-3-ethynylbenzene, (prepared essentially as described in PREPARATION 12), (133. 7 mg, 0. 98 mmol) in ethyl acetate (1 mL). Stir under nitrogen at room temperature for 18 h, filter through diatomaceous earth, wash with ethyl acetate and dichloromethane, and concentrate. Purify the residue by silica gel chromatography, eluting with 100 : 0 to 0 : 100 hexanes : dichloromethane. Treat with a 2 M solution of hydrogen chloride in diethyl ether to give the title compound (202 mg, 83%). 1H NMR (300 MHz, CH3 OH-d4) b 7. 51 (m, 2H), 7. 58 (m, 1H), 7. 68 (m, 1H), 8. 12 (m, 1H), 8. 74 (m, 1H), 8. 86 (br s, 1H), 9. 13 (br s, 1H) ; MS (ES) : m/z = 214 [M+H] +.

Reference： [1]Patent: WO2005/94822,2005,A1 .Location in patent: Page/Page column 65

29
[ 1120-90-7 ]
[ 6302-65-4 ]
4-[3]pyridylmercapto-benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With copper; potassium carbonate; In N,N-dimethyl-formamide; for 18h;Heating / reflux;	Intermediate 14; 4-(Pyridin-3-ylsulfanyl)-benzoic acid; Procedure N:; A mixture of 3-iodopyridine (823 mg, 4.01 mmol), methyl-4-mercaptobenzoate(500 mg, 2.97 mmol), potassium carbonate (677 mg, 4.90 mmol), and copper dust (4 mg, 0.653 mmol) in dimethylformamide (10 mL) are heated to reflux temperature for 18 h. The heat is removed and the reaction is filtered through Celite with dichloromethane. The filtrate is concentrated in vacuo and the residue is recrystallized from ether and hexane to obtain 689 mg (99%) of the title compound. MS (ES+) m/e 232.0 (M+l)+.

Reference： [1]Patent: WO2007/5503,2007,A1 .Location in patent: Page/Page column 40

30
[ 1120-90-7 ]
[ 6320-15-6 ]
[ 1000680-88-5 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 6016 - 6023

31
[ 1120-90-7 ]
[ 1826-11-5 ]
3-(2-phenylthiazol-5-yl)-pyridine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 7996 - 8000

32
[ 110-91-8 ]
[ 1120-90-7 ]
[ 2767-91-1 ]
[ 92670-29-6 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 4513 - 4516

33
[ 1120-90-7 ]
[ 23012-14-8 ]
[ 1014630-47-7 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 7383 - 7386

34
[ 1120-90-7 ]
[ 651358-83-7 ]
[ 106047-28-3 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 381 - 384

35
[ 288-13-1 ]
[ 1120-90-7 ]
[ 25700-12-3 ]

Yield	Reaction Conditions	Operation in experiment
83%	With copper(I) oxide; caesium carbonate; In dimethyl sulfoxide; at 100℃; for 24h;Inert atmosphere;	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 100C 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]Tetrahedron Letters,2009,vol. 50,p. 5868 - 5871
[2]Green Chemistry,2011,vol. 13,p. 42 - 45
[3]Tetrahedron,2013,vol. 69,p. 7279 - 7284

36
[ 1120-90-7 ]
[ 1066-54-2 ]
[ 80673-00-3 ]

Yield	Reaction Conditions	Operation in experiment
	With 5% palladium-copper on carbon; diethylamine; triphenylphosphine; In methanol; at 120℃; for 0.333333h;Inert atmosphere; Microwave irradiation;	General procedure: In a microwave reaction vessel, the iodide derivative (0.5mmol, 1.0 eq), PPh3 (5mol%), diethylamine (1.5mmol) and Pd-Cu/C catalyst (5mol% Pd) were suspended in MeOH (3mL). The tube was sealed with a Teflon cap, the reaction mixture was flushed under an argon flow for 5minand then TMSA (1mmol) was added. Then, the reaction mixture was stirred 120C under microwave irradiations for 20min. After completion of the reaction, the azide derivative (0.6mmol) was added and the mixture was irradiated again for 10minat 120C. The mixture was cooled to room temperature, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel.
	With bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) chloride; In dimethyl sulfoxide; at 20℃; for 1h;Inert atmosphere;	General procedure: A mixture of a (hetero)aryl iodide 1 (2.00 mmol), Pd(PPh3)2Cl2(28.1 mg, 0.04 mmol, 2 mol%), and CuCl (7.92 mg, 0.08 mmol, 4mol%) was dissolved in DMSO (1.00 mL) in a 8 mL microwavevessel equipped with a stirring bar and a septum and was degassedwith N2 for 5 min. After the addition of TMSA (0.42 mL,3.00 mmol) and anhydrous Et3N (0.55 mL, 4.00 mmol), the solutionwas stirred at r.t. for 1 h. Then, KF (232 mg, 4.00 mmol) wasadded and the reaction mixture was vigorously stirred under air inthe open reaction vessel at r.t. for 16 h. After the addition of themethanethiol 2 (or 6, 8) (1.20 mmol, 0.6 equiv), KOH (224 mg,4 mmol), and DMSO (1.00 mL), the mixture was heated in the microwavecavity at 130C for 1 h. After cooling to r.t., the solventswere removed under reduced pressure. The residue was absorbed onCelite and purified by column chromatography on silica gel with n-hexane or n-hexane-THF (100:1) as eluent. The experimental detailsare shown in Table 2.

Reference： [1]Journal of Medicinal Chemistry,2020
[2]Journal of Organic Chemistry,2014,vol. 79,p. 5586 - 5594
[3]Organic Letters,2013,vol. 15,p. 936 - 939
[4]ChemCatChem,2020,vol. 12,p. 1979 - 1984
[5]Synthesis,2009,p. 3527 - 3532
[6]Journal of Organometallic Chemistry,2014,vol. 755,p. 78 - 85
[7]Synthesis,2014,vol. 46,p. 3415 - 3422
[8]Journal of Medicinal Chemistry,2017,vol. 60,p. 7965 - 7983
[9]Journal of Organic Chemistry,2018,vol. 83,p. 8281 - 8291
[10]MedChemComm,2019,vol. 10,p. 263 - 267

37
[ 1120-90-7 ]
[ 273-75-6 ]
[ 1228149-78-7 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 2797 - 2799

38
[ 1120-90-7 ]
[ 201230-82-2 ]
[ 5467-74-3 ]
[ 14548-45-9 ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 2662 - 2667
[2]Chemistry - An Asian Journal,2019,vol. 14,p. 574 - 581
[3]European Journal of Organic Chemistry,2010,p. 6981 - 6986
[4]Synthesis,2011,p. 243 - 250

39
[ 288-13-1 ]
[ 1120-90-7 ]
[ 25700-12-3 ]
[ 25700-13-4 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 654 - 660

40
[ 1120-90-7 ]
potassium (trifluoromethyl)trimethoxyborate [ No CAS ]
[ 3796-23-4 ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 2689 - 2697

41
[ 1120-90-7 ]
(1,10-phenanthroline)(trifluoromethyl)copper(I) [ No CAS ]
[ 3796-23-4 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 3793 - 3798

42
[ 1120-90-7 ]
[ 471-25-0 ]
[ 59608-01-4 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 2214 - 2219

43
[ 1120-90-7 ]
[ 171596-36-4 ]
(6R,12aR)-6-Benzo[1,3]dioxol-5-yl-2-pyridin-3-yl-2,3,6,7,12,12a-hexahydro-pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 3222 - 3240

44
[ 1120-90-7 ]
[ 87199-17-5 ]
[ 127406-55-7 ]

Reference： [1]Advanced Synthesis and Catalysis,2011,vol. 353,p. 1889 - 1896

45
[ 1120-90-7 ]
[ 99-90-1 ]
[ 90395-45-2 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 7563 - 7568

46
[ 1120-90-7 ]
[ 1068471-18-0 ]
[ 1206628-90-1 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 6691 - 6703

47
[ 1120-90-7 ]
[ 1068471-18-0 ]
[ 1206628-91-2 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 6691 - 6703

48
[ 288-13-1 ]
[ 1120-90-7 ]
[ 25700-11-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	With copper(l) iodide; manganese(II) fluoride; (1R,2R)-1,2-diaminocyclohexane; potassium hydroxide; In water; at 100℃; for 48h;	General procedure: The N-nucleophile (1.47 mmol), CuI (Sigma-Aldrich, 99.999% purity, 0.147 mmol), MnF2 (Sigma-Aldrich, 98% purity, 0.441 mmol), KOH (2.94 mmol), the aryl halide (2.21 mmol), trans-1,2-diaminocyclohexane (0.294 mmol) and water (0.75 mL) 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 60C for 24 h. After cooling to room temperature, the mixture was diluted with dichloromethane and filtered through a pad of Celite. The combined organic extracts were dried with 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 known products was confirmed by 1H and 13C NMR spectroscopic analysis.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 7171 - 7174

49
[ 1120-90-7 ]
[ 108-95-2 ]
[ 2176-45-6 ]

Reference： [1]Journal of Catalysis,2017,vol. 348,p. 146 - 150
[2]Catalysis science and technology,2013,vol. 3,p. 2025 - 2031
[3]Synlett,2012,p. 101 - 106

50
[ 1120-90-7 ]
[ 252882-60-3 ]
C₂₂H₂₅N₃O₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 2945 - 2959

51
[ 1120-90-7 ]
[ 63680-90-0 ]
[ 1374320-71-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; N,N`-dimethylethylenediamine;copper dichloride; at 81℃; for 4h;	Step 2: Preparation of tert-butyl (3-chloro-1H-pyrazol-4-yl)carbamate Into a 2 L round bottom flask was added <strong>[63680-90-0]3-chloro-1H-pyrazol-4-amine hydrochloride</strong> (100 g, 649 mmol) and THF (500 mL). To this mixture were added di-tert-butyldicarbonate (156 g, 714 mmol) followed by sodium bicarbonate (120 g, 1429 mmol) and water (50.0 ml). The mixture was stirred for 16 h, diluted with water (500 mL) and ethyl acetate (500 mL) and transferred to a separatory funnel. This gave three layers; bottom-a white gelatinous precipitate, middle-light yellow aqueous, top-auburn organic. The phases were separated collecting the white gelatinous precipitate and the aqueous layer together. The aqueous was extracted with ethyl acetate (2200 mL) and the ethyl acetate extracts were combined, washed with brine (200 mL), dried over anhydrous sodium sulfate, filtered and rotary evaporated to give an auburn thick oil (160 g.). The thick oil was suspended in hexane (1000 mL) and stirred at 55 C. for 2 h. This gave a light brown suspension. The mixture was cooled to 0 C. and the solid collected by vacuum filtration and rinsed with hexane (210 mL). The sample was air dried to constant mass to afford (3-chloro-1H-pyrazol-4-yl)carbamate (102.97 g, 72% yield, 80% purity) as a light brown solid: mp 137-138 C.; 1H NMR (400 MHz, CDCl3) delta 10.69 (s, 1H), 7.91 (s, 1H), 1.52 (s, 9H).

Reference： [1]Patent: US2012/110702,2012,A1 .Location in patent: Page/Page column 22

52
[ 110-86-1 ]
[ 1120-90-7 ]
[ 581-50-0 ]
[ 4394-11-0 ]
[ 581-46-4 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 6702 - 6704

53
[ 1120-90-7 ]
[ 2567-81-9 ]
[ 6938-06-3 ]

Yield	Reaction Conditions	Operation in experiment
54%	With palladium diacetate; In 1-methyl-pyrrolidin-2-one; at 20 - 140℃; for 24.0h;Inert atmosphere;	General procedure: An oven-dried Schlenk-tube (10 mL) was charged with Pd source (1 mol percent), and ethyl potassium oxalate (0.75 mmol). The tube was evacuated and backfilled with argon (this procedure was repeated three times). After that, iodobenzene (0.5 mmol) and NMP (1.0 mL) were added by syringe under a counter flow of argon at room temperature. The reaction vessel was closed and then placed under stirring in a preheated oil bath. The reaction mixture was stirred for 24 h. Upon completion of the reaction, the mixture was cooled to room temperature and diluted with ethyl acetate, and analyzed by gas chromatography.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 5796 - 5799

54
[ 1120-90-7 ]
[ 271-44-3 ]
1-(pyridin-3-yl)-1H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With copper(I) oxide; caesium carbonate; In dimethyl sulfoxide; at 100℃; for 24h;Inert atmosphere;	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 100C 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]Chemistry - A European Journal,2017,vol. 23,p. 13676 - 13683
[2]Tetrahedron,2013,vol. 69,p. 7279 - 7284
[3]Synlett,2012,vol. 23,p. 2106 - 2110

55
[ 1120-90-7 ]
[ 939430-30-5 ]

Reference： [1]Patent: WO2012/140243,2012,A1

56
[ 1120-90-7 ]
[ 135039-77-9 ]
[ 3796-23-4 ]

Reference： [1]Helvetica Chimica Acta,2012,vol. 95,p. 2231 - 2236

57
[ 1120-90-7 ]
[ 936-49-2 ]
[ 1427476-02-5 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 3470 - 3475

58
[ 1120-90-7 ]
[ 141-97-9 ]
[ 39931-77-6 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 6767 - 6769

59
[ 1120-90-7 ]
[ 201230-82-2 ]
[ 67-64-1 ]
[ 3594-37-4 ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 12624 - 12628

60
[ 1120-90-7 ]
[ 85290-78-4 ]
[ 1286786-80-8 ]

Yield	Reaction Conditions	Operation in experiment
2.4 g	With copper(l) iodide; caesium carbonate; In N,N-dimethyl-formamide; at 120℃; for 4h;Inert atmosphere;	Step 1 Preparation of ethyl 3-methyl-1-(pyridin-3-yl)-1H-pyrazole-4-carboxylate 3.0 g of ethyl 3-methyl-1 H-pyrazole-4-carboxylate in 10 ml of N,N-dimethylformamide was mixed with 5.3 g of 3-iodopyridine, 990 mg of copper (I) iodide and 17.0 g of cesium carbonate successively. After the atmosphere in the reaction vessel was replaced by nitrogen gas, the mixture was stirred at 120C for 4 hours. After the reaction, the reaction mixture was mixed with 100 ml of water and extracted with ethyl acetate (150 ml × 1). The resulting organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane - ethyl acetate {1:1 (volume ratio, hereinafter the same applies)} as the eluent to give 2.4 g of the desired product as white crystals. 1H NMR(CDCl3 ,Me4 Si,300MHz)delta8.98(d,J=2.4Hz,1H),8.58(d,J=3.9Hz,1H), 8.38(s,1H),8.00-8.10(m, 1H),7.42(dd,J=4.8,8.1Hz,1H),4.34(q,J=7.2Hz,2H),2.57(s,3H), 1.38(t,J=7.2Hz,3H),(no detectable proton peaks for CO2 H)

Reference： [1]Patent: EP2674423,2013,A1 .Location in patent: Paragraph 0304

61
[ 1120-90-7 ]
[ 77152-08-0 ]
[ 3796-23-4 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 11126 - 11146
[2]Chemistry - A European Journal,2013,vol. 19,p. 17692 - 17697

62
[ 423165-07-5 ]
[ 1120-90-7 ]
[ 1616509-88-6 ]
[ 1616510-07-6 ]
[ 1616510-26-9 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); trifuran-2-yl-phosphane; potassium carbonate; In acetonitrile; at 80℃; for 3h;	General procedure: A mixture of trisallene 3 (0.25 mmol), aryl/heteroaryl iodides (0.90 mmol), nucleophiles (0.90 mmol), Pd2(dba)3 (7.5 mol %), TFP (tri-(2-furyl)phosphine) (30 mol %), and K2CO3 (2.25 mmol) in MeCN (5 mL) was stirred and heated at 80 C (oil bath temperature) until the starting material was completely consumed as monitored by TLC (see Table 1). The mixture was cooled and solvent removed under vacuo. The residue was dissolved in CHCl3 (25 mL) and extracted with H2O (20 mL) three times. The organic layer was dried over anhydrous MgSO4 and evaporated under rotatory evaporator to give the crude product, which was purified by flash chromatography.

Reference： [1]Tetrahedron,2014,vol. 70,p. 4934 - 4941

63
[ 1120-90-7 ]
[ 5720-07-0 ]
[ 5958-02-1 ]

Yield	Reaction Conditions	Operation in experiment
63%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; toluene; at 100℃; for 3h;Inert atmosphere;	To a solution of 3-iodopyridine (4.00 g, 19.50 mmol), 4-methoxy benzeneboronic acid (3.26 g, 21.50 mmol) in toluene (100 mL) and EtOH (25 mL) under nitrogen, was added 2 M aqueous sodium carbonate (29 mL, 58.50 mmol). The solution was degassed, tetrakis(triphenylphosphine) palladium (0) (750 mg, 0.65 mmol) was added and the reaction was heated at 100C for 3 hours. The mixture was allowed to cool to room temperature, diluted with EtOAc (50 mL), washed with water (2 x 50 mL), saturated brine (1 x 50 mL), dried (Na2S04) and concentrated in vacuo. The crude product was purified by column chromatography on silica eluting with DCM to afford 3-(4- methoxyphenyl)pyridine (2.43 g, 67 %) as an oil. 1H NMR (400 MHz, CHCI3- ) delta ppm 3.84 (s, 3 H) 6.98 - 7.02 (m, 2 H) 7.32-7.35 (m, 1 H) 7.49 - 7.53 (m, 2 H) 7.81 - 7.84 (m, 1 H) 8.54 (d, 7=4.09, 1 H) 8.81 (s, 1 H) MS ES+: 186

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 3946 - 3954
[2]Patent: WO2015/19103,2015,A1 .Location in patent: Page/Page column 51
[3]Chemistry - A European Journal,2016,vol. 22,p. 17407 - 17415

64
[ 1120-90-7 ]
[ 2140-11-6 ]
[ 1616667-82-3 ]

Yield	Reaction Conditions	Operation in experiment
54%	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

65
[ 1120-90-7 ]
[ 2176-45-6 ]

Reference： [1]ChemistryOpen,2014,vol. 3,p. 19 - 22
[2]ChemistryOpen,2014,vol. 3,p. 19 - 22

66
[ 1120-90-7 ]
[ 60753-14-2 ]

Reference： [1]Patent: WO2014/144836,2014,A2

67
[ 1120-90-7 ]
[ 33397-21-6 ]
[ 5958-02-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium phosphate; palladium diacetate; triphenylphosphine; In N,N-dimethyl-formamide; at 90℃; for 1h;Schlenk technique; Inert atmosphere;	General procedure: An oven dried Schlenk tube was purged with nitrogen and charged with 3-iodopyridine (0.875 mmol, 179.3 mg), BiPh3 (0.25 mmol, 110 mg), K3PO4 (1.5 mmol, 318 mg), Pd(OAc)2 (0.025 mmol, 5.6 mg), PPh3 (0.1 mmol, 26.2 mg) followed by dry DMF (3 mL) under nitrogen atmosphere. The reaction mixture was stirred in an oil bath at 90C for 1h. It was brought to rt, treated with water (10mL), and extracted with ethyl acetate (2×20 mL). The organic extract was treated with brine, dried over anhydrous MgSO4, and concentrated using rotary evaporator under the reduced pressure. The crude was subjected to silica gel column chromatography (5% EtOAc/Hexane) to obtain 3-phenylpyridine (1.1) as colorless oil (115 mg, 98%).

Reference： [1]Tetrahedron,2015,vol. 71,p. 338 - 349

68
[ 1120-90-7 ]
[ 17592-54-0 ]
[ 78348-28-4 ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 6537 - 6544

69
[ 1120-90-7 ]
[ 274-56-6 ]
[ 1383675-61-3 ]

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

70
[ 1120-90-7 ]
[ 75415-03-1 ]
[ 1286202-09-2 ]

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

71
[ 1120-90-7 ]
[ 470-17-7 ]
(4aS,8aR,9aS)-8a-methyl-5-methylidene-3-[(pyridin-3-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-3-yl)methylidene]decahydronaphtho[2,3-b]furan-2(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%; 63%	With palladium diacetate; potassium carbonate; 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). (3aR,4aS,8aR,9aR,E)-8a-Methyl-5-methylidene-3-[(pyridin-3-yl)methylidene]decahydronaphtho[2,3-b]furan-2(3H)-one (3a). Colorless crystals. Mp 207-209 (EtOH).[alpha]58927 +291 (c 1.23, CHCl3). IR spectrum, nu, cm-1: 712, 889,1000, 1172, 1215, 1423, 1657, 1737, 2830, 2911, 2929.UV spectrum, lambdamax, nm (log epsilon): 274 (4.20). 1H NMRspectrum, delta, ppm (J, Hz): 0.85 (3, s, 3); 1.26 (1H, ddd,J = 13.0, J = 12.7, J = 3.0, 1-HA); 1.42 (1H, dd, J = 13.9,J = 12.4) and 1.95 (1, ddd, J = 13.9, J = 6.6, J = 2.1,6-C2); 1.54 (1H, dd, J = 15.8, J = 4.8) and 2.25 (1H, dd,J =15.8, J = 1.6, 9-CH2); 1.55-1.62 (3, m, 1-CB,2-CH2); 1.91 (1H, d, J = 12.4, 5-CH); 2.01 (1H, ddd,J = 13.3, J = 13.1, J = 5.9) and 2.33 (1H, d, J = 13.3,3-CHB); 3.40 (1, ddd, J = 12.4, J = 6.2, J = 5.1, 7-C);4.38 (1, d, J = 1.3) and 4.75 (1, d, J = 1.3, 15-CB); 4.51(1, ddd, J = 5.1, J = 4.8, J = 1.6, 8-C); 7.36 (1,dd, J = 8.0, J = 4.8, H-5'); 7.38 (1, s, 13-C); 7.80 (1, ddd,J = 8.0, J = 1.9, J = 1.8, H-4'); 8.58 (1, dd, J = 4.8, J = 1.6,H-6'); 8.78 (1H, d, J = 1.8, H-2'). 13C NMR spectrum, delta, ppm:17.6 (H3); 22.6 (-2); 24.6 (C-6); 34.4 (C-10); 36.7 (-3);39.6 (-7); 41.2 (-9); 42.1 (-1); 46.3 (-5); 76.9 (-8);106.7 (-15); 123.8 (-5'); 130.2 (-11); 131.0 (-13);135.0 (-3'); 136.2 (-4'); 148.7 (-4); 150.1 (-6'); 150.3(-2'); 171.5 (-12). Found, %: C 77.67; H 7.44; N 4.53.C20H23NO2. Calculated, %: C 77.64; H 7.49; N 4.53.(4aS,8aR,9aS)-8a-Methyl-5-methylidene-3-[(pyridin-3-yl)methyl]-4a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]-furan-2(4H)-one (4a). Oily material. [alpha]58926 +132 (c 0.40,CHCl3). IR spectrum, nu, cm-1: 714, 891, 1016, 1026, 1045,1057, 1067, 1101, 1128, 1340, 1425, 1441, 1477, 1647,1680, 1751, 2851, 2864, 2932. UV spectrum, lambdamax, nm (log epsilon):222 (4.14), 257 (3.57), 263 (3.60), 269 (3.52). 1H NMRspectrum, delta, ppm (J, Hz): 0.82 (3, s, 3); 1.07 (1H, dd,J = 12.1, J = 11.8) and 2.25 (1, dd, J = 12.1, J = 6.3,9-C2); 1.24 (1, ddd, J = 14.7, J = 13.7, J = 4.4, 1-CA);1.50-1.59 (3H, m, 1-CB, 2-C2); 1.76 (1, d, J =13.0, 5-C);1.88 (1, ddd, J = 14.5, J = 13.5, J = 4.6, 3-CA); 2.27-2.31 (2, m, 3-CB, 6-CA); 2.71 (1, dd, J = 14.0,J = 3.6, 6-CB); 3.50 (1, d, J = 15.0) and 3.56 (1, d,J = 15.0, 13-C2); 4.50 (1, d, J = 1.5) and 4.79 (1, d,J = 1.5, 15-C2); 4.81 (1, dd, J = 11.8, J = 6.3, 8-C);7.15 (1, dd, J = 7.8, J = 4.5, H-5'); 7.55 (1, d, J = 7.8,H-4'); 8.38 (1, d, J = 4.5, H-6'); 8.39 (1H, s, H-2'). 13C NMRspectrum, delta, ppm: 16.2 (CH3); 22.0 (-2); 25.6 (-6); 26.3(-13); 35.9 (-3); 36.7 (-10); 40.4 (-1); 47.3 (-9);49.8 (-5); 77.9 (-8); 106.8 (-15); 122.4 (-11); 123.4(-5'); 133.7 (-3'); 135.9 (-4'); 147.6 (-6'); 147.8(-4); 149.3 (-2'); 164.2 (-7); 173.4 (-12). Massspectrum, m/z (Irel, %): 310 (24), 309 [M]+ (100), 308 (31),294 (23), 264 (11), 130 (11), 93 (14), 92 (10), 91 (10), 77(10). Found, m/z: 309.1722 [M]+. C20H23NO2. Calculated,m/z: 309.1723.

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

72
[ 1120-90-7 ]
[ 470-17-7 ]
(3aR,4aS,8aR,9aR,E)-8a-methyl-5-methylidene-3-[(pyridin-3-yl)methylidene]decahydronaphtho[2,3-b]furan-2(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	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). (3aR,4aS,8aR,9aR,E)-8a-Methyl-5-methylidene-3-[(pyridin-3-yl)methylidene]decahydronaphtho[2,3-b]furan-2(3H)-one (3a). Colorless crystals. Mp 207-209 (EtOH).[alpha]58927 +291 (c 1.23, CHCl3). IR spectrum, nu, cm-1: 712, 889,1000, 1172, 1215, 1423, 1657, 1737, 2830, 2911, 2929.UV spectrum, lambdamax, nm (log epsilon): 274 (4.20). 1H NMRspectrum, delta, ppm (J, Hz): 0.85 (3, s, 3); 1.26 (1H, ddd,J = 13.0, J = 12.7, J = 3.0, 1-HA); 1.42 (1H, dd, J = 13.9,J = 12.4) and 1.95 (1, ddd, J = 13.9, J = 6.6, J = 2.1,6-C2); 1.54 (1H, dd, J = 15.8, J = 4.8) and 2.25 (1H, dd,J =15.8, J = 1.6, 9-CH2); 1.55-1.62 (3, m, 1-CB,2-CH2); 1.91 (1H, d, J = 12.4, 5-CH); 2.01 (1H, ddd,J = 13.3, J = 13.1, J = 5.9) and 2.33 (1H, d, J = 13.3,3-CHB); 3.40 (1, ddd, J = 12.4, J = 6.2, J = 5.1, 7-C);4.38 (1, d, J = 1.3) and 4.75 (1, d, J = 1.3, 15-CB), 4.51 (1, ddd, J = 5.1, J = 4.8, J = 1.6, 8-C); 7.36 (1,dd, J = 8.0, J = 4.8, H-5'); 7.38 (1, s, 13-C); 7.80 (1, ddd,J = 8.0, J = 1.9, J = 1.8, H-4'); 8.58 (1, dd, J = 4.8, J = 1.6,H-6'); 8.78 (1H, d, J = 1.8, H-2'). 13C NMR spectrum, delta, ppm:17.6 (H3); 22.6 (-2); 24.6 (C-6); 34.4 (C-10); 36.7 (-3);39.6 (-7); 41.2 (-9); 42.1 (-1); 46.3 (-5); 76.9 (-8);106.7 (-15); 123.8 (-5'); 130.2 (-11); 131.0 (-13);135.0 (-3'); 136.2 (-4'); 148.7 (-4); 150.1 (-6'); 150.3(-2'); 171.5 (-12). Found, %: C 77.67; H 7.44; N 4.53.C20H23NO2. Calculated, %: C 77.64; H 7.49; N 4.53.

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

73
[ 1120-90-7 ]
[(2,2'-bipyridine)₂Cu][O₂CCF₂Cl] [ No CAS ]
[ 3796-23-4 ]

Reference： [1]RSC Advances,2016,vol. 6,p. 75465 - 75469

74
[ 1120-90-7 ]
[ 2488-14-4 ]
N-α-boc-1-(3-pyridyl)-L-histidine methyl ester [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 8937 - 8941

75
[ 1120-90-7 ]
[ 3250-74-6 ]

Reference： [1]Monatshefte fur Chemie,2016,vol. 147,p. 2135 - 2142

76
[ 1120-90-7 ]
[ 58093-05-3 ]
8-(pyridin-3-yl-iodanylidene)-6,10-dioxaspiro[4.5]decane-7,9-dione [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 453 - 458

77
[ 1120-90-7 ]
[ 16282-16-9 ]
1,2-diphenyl-1-(pyridin-3-yl)butan-1-ol [ No CAS ]

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

78
[ 1120-90-7 ]
[ 533-58-4 ]
[ 84284-70-8 ]
3-(2-(4-(benzyloxy)phenyl)benzofuran-3-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%		General procedure: To a solution of the 2-Iodo-5-methoxyphenol (1mmol, 252mg) and the 4-Ethynylanisole (1.2 equiv., 166mg) in dry THF (1.6mL, 0.6M of the Iodophenol), at 0C under N2, was added CH3MgBr (THF solution, 2.3M, 2 equiv., 0.792mL) dropwise. The mixture was allowed to warm to room temperature, and Pd(Ph3P)2Cl (3mol%, 21.3mg) was added before the mixture was heated to 65C for 2h under N2. The reaction mixture was then cooled to room temperature and the THF was removed under reduced pressure. DMSO (2mL) was added to the residue followed by addition of 2-Fluoro-4-iodopyridine (1.2 equiv., 269.7mg) and the mixture was heated to 80C for 4h under N2. The mixture was cooled to room temperature and diluted with EtOAc, washed with H2O and brine. The organic phase was dried over Na2SO4, concentrated and purified on silica followed by preparative HPLC (25?100% B over 25min).

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 143,p. 1077 - 1089

79
[ 1120-90-7 ]
[ 71-44-3 ]
N¹,N^1'-(butane-1,4-diyl)bis[N³-(pyridin-3-yl)propane-1,3-diamine] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With copper(l) iodide; 2-(2-methyl-1-oxopropyl)cyclohexanone; caesium carbonate; In N,N-dimethyl-formamide; at 110℃; for 24h;Inert atmosphere;	General procedure: A two-neck flask equipped with a reflux condenser and a magnetic stir bar was charged with 2 or 3iodopyridine (256-512 mg,1.25-2.5 mmol) (for hetarylation of polyamines, 2-bromopyridine (395 mg, 2.5 mmol) was used), CuI (9.5-19 mg,0.05-0.1 mmol), 2-isobutyrylcyclohexanone (17-33 mg,0.1-0.2 mmol), the corresponding diamine or polyamine(0.5-1 mmol), cesium carbonate (420-840 mg, 1.25-2.5 mmol),and DMF (1-2 mL) under argon. The stirred reaction mixture was heated at 140 C for 24 h, cooled, diluted with dichloromethane (5 mL) and filtered. The precipitate was washed with dichloromethane (5 mL), the combined organic phases were concentrated in vacuo. The residue was dissolved in dichloromethane (5 mL), washed with water (5 mL), dried over anhydrous sodium sulfate, and concentrated in vacuo. Purification of the residue by silica gel column chromatography (gradient elution with CH2Cl2-petroleum ether (1 : 4)?(4 : 1),CH2Cl2, CH2Cl2-MeOH (100 : 1)?(3 : 1), CH2Cl2-MeOH-NH3(aq)) afforded the title products as crystalline or oily substances.

Reference： [1]Russian Chemical Bulletin,2017,vol. 66,p. 1611 - 1617
Izv. Akad. Nauk, Ser. Khim.,2017,p. 1611 - 1617,7

80
[ 1120-90-7 ]
[ 3476-89-9 ]
4-(3-pyridyl)-2,3-dihydro-1H-quinoxaline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63.5%	With RuPhos Pd G4; sodium t-butanolate; ruphos; In 1,4-dioxane; at 80℃; for 12h;Inert atmosphere;	A round bottomed flask was charged with <strong>[3476-89-9]1,2,3,4-<strong>[3476-89-9]tetrahydroquinoxaline</strong></strong> (500.0mg, 3.7 mmol, 1.0 eq), 3-iodopyridine (840.3 mg, 4.1 mmol, 1.1 eq), RuPhos (173.9 mg, 372.6umol, 0.1 eq), RuPhos-Pd-G4 (313.8 mg, 372.6 umol, 0.1 eq), and tBuONa(1.1 g, 11.2 mmol, 3.0 eq). Dioxane (8 mL) was added, and the reaction mixture was evacuated and refilled 3 times with nitrogen before being stirred at 80 C for 12 h. LCMS indicated one main desired spot formed. The reaction mixture was concentrated in vacuo and purified by flash silica gelchromatography (eluting with dichloromethane and methanol) to afford 4-(3-pyridyl)-2,3- dihydro-1H-quinoxaline (0.5 g, 63.5% yield) as a black brown solid.

Reference： [1]Patent: WO2018/81091,2018,A1 .Location in patent: Paragraph 0219

81
[ 1120-90-7 ]
[ 201230-82-2 ]
[ 39549-79-6 ]
7-methyl-2-(pyridin-3-yl)quinazolin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 120℃; under 7500.75 Torr; for 20h;Inert atmosphere; Autoclave;	General procedure: A 12mL vial was charged with MCM-41-2P-Pd(OAc)2 (2molpercent), 2-aminobenzamide (1mmol), aryl iodide (1mmol) (if solid) and a stirring bar. Then, DMF (2mL), aryl iodide (1mmol) (if liquid) and DBU (2mmol) were injected by syringe under an argon atmosphere. The vial was placed in an alloy plate, which was transferred into a 300mL Parr Instruments 4560 series autoclave under an argon atmosphere. After flushing the autoclave three times with CO, a pressure of 10bar CO was fixed at ambient temperature. The autoclave was heated for 20hat 120°C. After completion of the reaction, the autoclave was cooled to room temperature and the pressure was released carefully. The reaction mixture was diluted with ethyl acetate (10mL) and filtered. The palladium catalyst was washed with distilled water (2×5mL) and acetone (2×5mL), and reused in the next run. The filtrate was concentrated in vacuo and the pure product was isolated by either washed with water, ethyl acetate and finally hexane or recrystallization from MeOH.

Reference： [1]Journal of Organometallic Chemistry,2018,vol. 875,p. 35 - 45

82
[ 1120-90-7 ]
[ 18599-22-9 ]
3-(1,1,2,2-tetrafluorobut-3-en-1-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%		General procedure: In a two-necked round-bottomed flask, equipped with a teflon-coated stirrer bar and reflux condenser, was added ethyl 2-iodobenzoate (3j, 0.14 g 0.50 mmol), Cu2O (0.060 g, 0.42 mmol), and a DMF solution of 2-Zn (0.65 M, 1.54 mL, 1.0 mmol), and the mixture was stirred at 100 C for 24 h. After being cooled to room temperature, the resulting solution was subjected to a short pad of silica gel using hexanes as an eluent. The filtrate was concentrated in vacuo to give the crude materials, which was purified by silica gel column chromatography to provide the corresponding compound 4j (0.13 g, 0.48 mmol) in 96% yield as an yellow oil.

Reference： [1]Beilstein Journal of Organic Chemistry,2018,vol. 14,p. 2375 - 2383

83
[ 1120-90-7 ]
[ 103438-84-2 ]
2-fluoro-5-(pyridin-3-yloxy)benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14%	With copper(l) iodide; N,N-dimethylglycine hydrochoride; caesium carbonate; In 1,4-dioxane; at 90℃; for 16h;Inert atmosphere; Sealed tube;	[00281] To a stirred solution of <strong>[103438-84-2]2-fluoro-5-hydroxybenzaldehyde</strong> (3 g, 21.4 mmol) in 1,4- dioxane (30 mL) at rt, were added 3-iodopyridine ( 4.85 g, 23.5 mmol), Cs2C03 (12.9 g, 42.8 mmol), Cul (910 mg, 4.28 mmol) and N,N-dimethylglycine hydrochloride (2.62 g, 18.7 mmol). The reaction mixture was sealed under an inert atmosphere and heated at 90 C for 16 h. The reaction mixture was cooled to rt and filtered through a pad of celite. The celite was further washed with EtOAc (2 x 100 mL). The combined filtrates were dried (Na2S04), filtered, and concentrated under reduced pressure. The residue was purified (silica gel; eluting with 0-100% EtOAc in hexane) to afford compound 1 (660 mg, 14%) as an off-white solid. 1H NMR (400 MHz, CDC13) delta 10.33 (s, 1H), 8.39 - 8.45 (m, 2H), 7.46 (m, 1H), 7.28 - 7.34 (m, 3H), 7.23 (m, 1H).

Reference： [1]Patent: WO2018/183122,2018,A1 .Location in patent: Paragraph 00280; 00281

84
[ 1120-90-7 ]
[ 1892-22-4 ]
[ 201230-82-2 ]
[ 1352127-79-7 ]

Yield	Reaction Conditions	Operation in experiment
36%	With palladium diacetate; triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 50℃; under 750.075 Torr; for 24h;	General procedure: In a typical experiment Pd(OAc)2 (2.81 mg, 0.0125 mmol), triphenylphosphine (6.55 mg, 0.025 mmol) or Xantphos (7.23 mg, 0.0125 mmol), iodoalkene (1-5) or iodo(hetero)arene (6-11) substrates (0.5 mmol), and 3-aminolactams (3-amino-azepan-2-one (a), <strong>[1892-22-4]3-amino-piperidin-2-one</strong> (b), 3-amino-pyrrolidin-2-one (c)) (0.55 mmol) and triethylamine (0.25 mL) were dissolved in DMF (5 mL) under argon in a 100 mL three-necked flask equipped with reflux condenser connected to a balloon filled with argon. The atmosphere was changed to carbon monoxide. The reaction was conducted for the given reaction time upon stirring at 50 C and analyzed by Gc and GC-MS. The cooled reaction mixture was then distilled to dryness under reduced pressure. The residue was dissolved in chloroform (15 mL) and washed twice with water (15 mL). The organic phase was dried over Na2SO4, filtered and evaporated under reduced pressure to a solid material. All compounds (except 10a, 10b) were subjected to column chromatography (Silicagel 60 (Sigma), 0.063-0.200 mm) or Aluminum oxide (Sigma), activated, neutral, Brockmann activity I), CHCl3/MeOH or CHCl3/EtOH eluent mixtures (the exact ratios are specified in Characterization (3.4) for each compound). In the case of 10a and 10b chloroform (10 mL) was added to the residue and the insoluble material (product) was filtered and dried.

Reference： [1]Tetrahedron,2018,vol. 74,p. 6116 - 6128

85
[ 1120-90-7 ]
[ 7150-72-3 ]
[ 215305-99-0 ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 4147 - 4153

86
[ 1120-90-7 ]
[ 73286-71-2 ]
[ 874218-24-3 ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 4147 - 4153

87
[ 1120-90-7 ]
[ 2923-18-4 ]
[ 3796-23-4 ]

Reference： [1]Organic Process Research and Development,2019,vol. 23,p. 2345 - 2353

88
[ 1120-90-7 ]
[ 59608-01-4 ]

Reference： [1]Patent: WO2020/114494,2020,A1

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
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P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
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P233	Keep container tightly closed.
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P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
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P273	Avoid release to the environment.
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.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
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Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
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P307	IF exposed:
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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:
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P372	Explosion risk in case of fire.
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P378
P380	Evacuate area.
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
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P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
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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.
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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:
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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.
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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.
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P411 + P235	Keep cool.
Disposal
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P501	Dispose of contents/container to ...
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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
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H228	Flammable solid
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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
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H331	Toxic if inhaled
H332	Harmful if inhaled
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H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
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H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
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H351	Suspected of causing cancer
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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

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[ 1120-90-7 ] Synthesis Path-Upstream 1~42

[ 1120-90-7 ] Synthesis Path-Downstream 1~88

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Pyridines

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