[ CAS No. 7295-76-3 ] {[proInfo.proName]}

Name: 7295-76-3|3-Methoxypyridine|98%
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Quality Control of [ 7295-76-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 7295-76-3 ]

Product Details of [ 7295-76-3 ]

CAS No. :	7295-76-3	MDL No. :	MFCD00673022
Formula :	C₆H₇NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UMJSCPRVCHMLSP-UHFFFAOYSA-N
M.W :	109.13	Pubchem ID :	23719
Synonyms :	β-Methoxypyridine

Calculated chemistry of [ 7295-76-3 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	30.73
TPSA :	22.12 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.56
Log Po/w (XLOGP3) :	0.99
Log Po/w (WLOGP) :	1.09
Log Po/w (MLOGP) :	0.13
Log Po/w (SILICOS-IT) :	1.4
Consensus Log Po/w :	1.03

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.63
Solubility :	2.56 mg/ml ; 0.0235 mol/l
Class :	Very soluble
Log S (Ali) :	-1.04
Solubility :	9.88 mg/ml ; 0.0906 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.09
Solubility :	0.891 mg/ml ; 0.00817 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.38

Safety of [ 7295-76-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H227-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 7295-76-3 ]

* 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 [ 7295-76-3 ]
Downstream synthetic route of [ 7295-76-3 ]

[ 7295-76-3 ] Synthesis Path-Upstream 1~9

1
[ 7295-76-3 ]
[ 4045-29-8 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1947, p. 341 344

2
[ 7295-76-3 ]
[ 576-83-0 ]
[ 1849-53-2 ]

Reference： [1] Patent: US5554620, 1996, A,

3
[ 7295-76-3 ]
[ 68-12-2 ]
[ 1849-53-2 ]

Reference： [1] Journal of Organic Chemistry, 1990, vol. 55, # 1, p. 69 - 73
[2] Tetrahedron Letters, 1988, vol. 29, # 7, p. 773 - 776

4
[ 7295-76-3 ]
[ 52605-96-6 ]

Yield	Reaction Conditions	Operation in experiment
10.20 g	With hydrogenchloride; potassium permanganate In water at 0 - 15℃;	(1) Dissolving 10.91 g (0.1 mol) of 3-methoxypyridine in 121.53 g (containing 1.0 mol of hydrogen chloride) of 30.0percent hydrochloric acid,Under stirring, the temperature was controlled at 0-15° C., and 11.83 g of a 25.0percent potassium manganate solution was added dropwise. After the dropwise addition was completed, the reaction temperature was controlled at 0-15° C. to carry out the chlorination reaction of the reaction system.During the reaction, samples were taken at regular intervals and detected with high performance liquid chromatography.When it was detected that the mass of 2-chloro-3-methoxypyridine in the reaction system accounted for 80.5percent of the total mass of organic substances in the reaction system,The reaction was terminated by adding 11.36 g (0.06 mol) of stannous chloride to obtain a feed solution containing 2-chloro-3-methoxypyridine; (2) 71.8 g of methylene chloride was added to the reaction mixture, and the mixture was stirred and extracted for 2 hours. The mixture was allowed to stand for 1 hour and the organic phase was taken and allowed to cool down to -15°C to -5°C.The solids were extracted and analyzed from the organic phase. The resulting 10.20 g of solid was 2-chloro-3-methoxypyridine. The yield was calculated to be 71percent. After the determination, the main content was 98.0percent.

Reference： [1] Patent: CN107954913, 2018, A, . Location in patent: Paragraph 0018

5
[ 7295-76-3 ]
[ 10201-71-5 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1955, vol. 74, p. 1171,1174
[2] Journal of the American Chemical Society, 1947, vol. 69, p. 1147,1148

6
[ 7295-76-3 ]
[ 52334-90-4 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1955, vol. 74, p. 1160,1164

7
[ 7295-76-3 ]
[ 113118-83-5 ]

Reference： [1] Heterocycles, 1987, vol. 26, # 8, p. 2159 - 2164

8
[ 7295-76-3 ]
[ 909717-95-9 ]

Reference： [1] Patent: WO2016/101119, 2016, A1,

9
[ 7295-76-3 ]
[ 163234-74-0 ]

Reference： [1] Science, 2013, vol. 342, # 6161, p. 956 - 960

[ 7295-76-3 ] Synthesis Path-Downstream 1~88

1
[ 7295-76-3 ]
[ 4045-29-8 ]

Reference： [1]Bulletin de la Societe Chimique de France,1947,p. 341 344
[2]Chemical Science,2019,vol. 10,p. 2193 - 2198

2
[ 7295-76-3 ]
[ 14906-61-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With dihydrogen peroxide; acetic anhydride In water at 80℃; for 12h;
82%	With formic acid; urea at 20℃; for 6h;
73%	With 3-chloro-benzenecarboperoxoic acid; sodium sulfite In dichloromethane at 20℃; for 0.166667h; Inert atmosphere;	212.1 [00659] Step 1: To a solution of 3-methoxy-pyridine (5.0 g, 45.8 mmol) in DCM (100 mL) was added m-CPBA (15.0 g, 68.7 mmol). The resulting mixture was stirred at room temperature overnight. Then Na2S03 (excess) was added into the reaction mixture and the mixture was stirred for 10 mins. The organic phase was collected and concentrated to give 3-methoxy-pyridine 1 -oxide (4.2 g, yield: 73%) as a white solid, which was used for next step without further purification. lH NMR (400 MHz, CDC13) : δ = 7.98 (t, J= 2.0 Hz, 1H), 7.93-7.87 (m, 1H), 7.16 (dd, J= 8.4, 6.4 Hz, 1H), 6.88 (s, dd, J= 8.8, 1.6 Hz, 1H), 3.85 (s, 3H).

68%	With urea hydrogen peroxide; trifluoroacetic anhydride In acetonitrile at 20℃; for 18h;
40%	With 3-chloro-benzenecarboperoxoic acid In chloroform 1.) RT, 2 h, 2.) reflux, 1 h;
34%	With dihydrogen peroxide; acetic acid at 80℃; for 5h; Inert atmosphere;	63.1 first step3-methoxypyridine N-oxide The compound 3-methoxypyridine 63a (1.1 g, 10.0 mmol) was dissolved in acetic acid (20 mL) and hydrogen peroxide was added at room temperature.(2.0 mL, 30%, 20.0 mmol), stirred at 80 ° C for 5 hours. The mixture was concentrated and added to aq. NaOH (4M) to pHThe value is greater than 8, extracted with dichloromethane (3 × 10 mL), washed with 100 mL of water, dried over anhydrous sodium sulfate, filtered and concentratedThe net product was 3-methoxypyridine N-oxide 63b (0.42 g, 3.4 mmol, white solid).
	With water; dihydrogen peroxide; acetic acid at 95℃;
	With dihydrogen peroxide In dichloromethane; acetic acid	A A. A. 3-Methoxypyridine-1-oxide (762A) 3-Methoxypyridine (20.08 g, 209 mmol) was dissolved in 100 mL of acetic acid. 30% H2O2 (28.3 mL, 275 mmol) was added and the reaction mixture was heated at 70° C. for six h. The cooled reaction mixture was concentrated and the residue dissolved in CH2Cl2 and stirred overnight with 20 g of solid potassium carbonate. The mixture was filtered and concentrated to give compound 762A (25.2 g, 100%) as a light yellow solid which was characterized by 1H NMR and carried on to the next step.

Reference： [1]Rassadin, Valentin A.; Zimin, Dmitry P.; Raskil'dina, Gulnara Z.; Ivanov, Alexander Yu.; Boyarskiy, Vadim P.; Zlotskii, Semen S.; Kukushkin, Vadim Yu. [Green Chemistry, 2016, vol. 18, # 24, p. 6630 - 6636]
[2]Balicki, Roman; Golinski, Jerzy [Synthetic Communications, 2000, vol. 30, # 8, p. 1529 - 1534]
[3]Current Patent Assignee: SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE - WO2015/200534, 2015, A2 Location in patent: Paragraph 00659
[4]Keith, John M. [Journal of Organic Chemistry, 2008, vol. 73, # 1, p. 327 - 330]
[5]Sato, Nobuhiro; Nagano, Eiichi [Journal of Heterocyclic Chemistry, 1993, vol. 30, # 3, p. 691 - 698]
[6]Current Patent Assignee: NANJING INNOCARE PHARMA TECH; SYNERCARE PHARMA TECH - CN109020957, 2018, A Location in patent: Paragraph 0262
[7]Prins [Recueil des Travaux Chimiques des Pays-Bas, 1957, vol. 76, p. 58,61]
[8]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2004/77605, 2004, A1

3
[ 7295-76-3 ]
[ 20265-37-6 ]

Reference： [1]Journal of the American Chemical Society,1947,vol. 69,p. 1147,1148
[2]Journal of the American Chemical Society,1947,vol. 69,p. 1147,1148

4
[ 7295-76-3 ]
[ 2926-30-9 ]
[ 135182-80-8 ]

Yield	Reaction Conditions	Operation in experiment
62%	With fluorine; sodium fluoride In acetonitrile at -40℃; for 3h;

Reference： [1]Umemoto, Teruo; Harasawa, Kikuko; Tomizawa, Ginjiro; Kawada, Kosuke; Tomita, Kyoichi [Bulletin of the Chemical Society of Japan, 1991, vol. 64, # 4, p. 1081 - 1092]

5
[ 7295-76-3 ]
[ 6414-69-3 ]
[ 541-41-3 ]
4-(2-Ethoxycarbonyl-ethyl)-3-methoxy-4H-pyridine-1-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 3162 - 3164

6
[ 7295-76-3 ]
[ 36016-40-7 ]
[ 81211-83-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	In dichloromethane for 0.5h; Ambient temperature;
	In dichloromethane at 0 - 20℃; for 1h;	The wet filter cake of MSH was dissolved in CH2Cl2; the organic layer was separated and quickly dried over MgSO4. The resulting solution of MSH was slowly added to a stirred solution of 9 (5.06 g, 34.0 mmol) in CH2Cl2 (10 mL) at 0 oC. After stirring for 1 h at room temperature, the reaction mixture was concentrated in vacuo to give the piridinium salt as a brown oil.
	In dichloromethane at 0℃; Inert atmosphere; Reflux;

Reference： [1]Kurita; Kojima; Enkaku; Tsuchiya [Chemical and Pharmaceutical Bulletin, 1981, vol. 29, # 12, p. 3696 - 3705]
[2]Ochiai, Koji; Takita, Satoshi; Kojima, Akihiko; Eiraku, Tomohiko; Ando, Naoki; Iwase, Kazuhiko; Kishi, Tetsuya; Ohinata, Akira; Yageta, Yuichi; Yasue, Tokutaro; Adams, David R.; Kohno, Yasushi [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 18, p. 5833 - 5838]
[3]Wang, Amu; Liu, Ya-Zhou; Shen, Zhongke; Qiao, Zeen; Ma, Xiaofeng [Organic Letters, 2022, vol. 24, # 7, p. 1454 - 1459]

7
[ 7295-76-3 ]
[ 68-12-2 ]
[ 1849-53-2 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 69 - 73
[2]Tetrahedron Letters,1988,vol. 29,p. 773 - 776

8
[ 7295-76-3 ]
[ 109-00-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With toluene-4-sulfonic acid; lithium chloride In 1-methyl-pyrrolidin-2-one at 180℃; for 1h;
89%	With L-Selectride In tetrahydrofuran for 24h; Reflux; Inert atmosphere; chemoselective reaction;	Demethylation of Methoxypyridines; General Procedure: General procedure: Toa solution of 1 (1.00 mmol) in THF (7.0 mL) was added L-selectride(1 M in THF, 3.0 mL, 3.00 mmol, 3 equiv) under an argonatmosphere. After being refluxed and monitored by TLC, thereaction mixture was quenched with MeOH and evaporated invacuo. The residue was purified by silica gel column chromatographyto give the desired compound 2.
61%	With hexamethyldisilathiane; sodium methylate In various solvent(s) at 180℃; for 24h;

With trimethylammonium heptachlorodialuminate In dichloromethane Heating;

Reference： [1]Location in patent: experimental part Soni, Ajay; Dutt, Akhilesh; Sattigeri, Viswajanani; Cliffe, Ian A. [Synthetic Communications, 2011, vol. 41, # 12, p. 1852 - 1857]
[2]Makino, Kosho; Hasegawa, Yumi; Inoue, Takahide; Araki, Koji; Tabata, Hidetsugu; Oshitari, Tetsuta; Ito, Kiyomi; Natsugari, Hideaki; Takahashi, Hideyo [Synlett, 2019, vol. 30, # 8, p. 951 - 954]
[3]Shiao, Min-Jen; Ku, Wei-Shen; Hwu, Jih Ru [Heterocycles, 1993, vol. 36, # 2, p. 323 - 328]
[4]Kemperman, Gerardus J.; Roeters, Theodorus A.; Hilberink, Peter W. [European Journal of Organic Chemistry, 2003, # 9, p. 1681 - 1686]

9
[ 14906-61-7 ]
[ 7295-76-3 ]

Yield	Reaction Conditions	Operation in experiment
96.66%	With iron(III) chloride; pyrographite; hydrazine hydrate In ethanol at 70℃; for 4h;	1.3 (3) Preparation of 3-methoxypyridine Into a 500 ml three-neck flask were respectively added 25g activated carbon, 1 mol/L ferric chloride ethanol solution 75 ml. After stirring 15min, then add 62.5g (0.5 mol) N-oxido-3-methoxypyridine. Heat to 70 °C. Add dropwise 80% hydrazine hydrate 62.5g (1.0 mol). About 1h dropping complete. Maintain temperature and stir for 3h. Afterwards, cool to room temperature, filtered activated carbon, absolute ethanol and washing the filter cake, the filtrate, recovering the ethanol, vacuum distillation 52.68g 3-methoxypyridine, yield 96.66%.
90%	With sodium tetrahydroborate; zirconium(IV) chloride In tetrahydrofuran at 0 - 35℃; for 0.25h;
90%	With sodium tetrahydroborate; lithium chloride In tetrahydrofuran at 35℃; for 0.5h;

88%	With sodium hypophosphite In acetic acid at 60℃; for 2h;
82%	With sodium hydroxide; thiourea S,S-dioxide In ethanol at 80 - 85℃; for 2.5h;
81%	With ammonium formate In methanol at 40℃; for 0.333333h;
68%	With ammonium formate; zinc In methanol for 6h; Heating;
65%	With ammonium formate In methanol at 50℃; for 4h;

Reference： [1]Current Patent Assignee: ANHUI UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN106632006, 2017, A Location in patent: Paragraph 0023
[2]Chary, K. Purushothama; Mohan, G. Hari; Iyengar, D. S. [Chemistry Letters, 1999, # 12, p. 1339 - 1340]
[3]Raja Ram; Purushothama Chary; Iyengar [Synthetic Communications, 2000, vol. 30, # 19, p. 3511 - 3515]
[4]Balicki, Roman; Kaczmarek, Lukasz [Gazzetta Chimica Italiana, 1994, vol. 124, # 9, p. 385 - 386]
[5]Balicki, Roman; Chmielowiec, Urszula [Monatshefte fur Chemie, 2000, vol. 131, # 10, p. 1105 - 1107]
[6]Balicki, Roman [Synthesis, 1989, # 8, p. 645 - 646]
[7]Balicki, Roman; Cybulski, Marcin; Maciejewski, Grzegorz [Synthetic Communications, 2003, vol. 33, # 23, p. 4137 - 4141]
[8]Balicki, Roman; Maciejewski, Grzegorz [Synthetic Communications, 2002, vol. 32, # 11, p. 1681 - 1683]

10
[ 7295-76-3 ]
[ 74-88-4 ]
[ 52693-54-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	In acetonitrile Inert atmosphere; Reflux;
62%	In diethyl ether at 70℃;
	Heating;

In diethyl ether at 20℃;

Reference： [1]Chen, Hua; Fu, Haiyan; Li, Ruixiang; Li, Wenjing; Luo, Lihua; Sun, Rui; Tang, Juan; Yuan, Maoling; Zheng, Xueli [Organic Letters, 2022, vol. 24, # 15, p. 2821 - 2825]
[2]Penkett, Clive S.; Simpson, Iain D. [Tetrahedron, 1999, vol. 55, # 19, p. 6183 - 6204]
[3]Penkett; Simpson [Synlett, 1999, # 1, p. 93 - 95]
[4]Location in patent: experimental part Huang, Sha; Wong, Jesse C.S.; Leung, Adam K.C.; Chan, Yee Man; Wong, Lili; Fernendez, Myrien R.; Miller, Amanda K.; Wu, Weiming [Tetrahedron Letters, 2009, vol. 50, # 35, p. 5018 - 5020]

11
[ 7295-76-3 ]
HNO₃+H₂SO₄ [ No CAS ]
[ 20265-37-6 ]

Reference： [1]Journal of the American Chemical Society,1947,vol. 69,p. 1147,1148

12
[ 7295-76-3 ]
[ 67670-69-3 ]
N-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosyl)onate]-3'-methoxypyridinium tetrafluoroborate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With silver tetrafluoroborate In tetrahydrofuran at 5℃; for 48h;

Reference： [1]Chou, Doug T. H.; Watson, Jacqueline N.; Scholte, Andrew A.; Borgford, Thor J.; Bennet, Andrew J. [Journal of the American Chemical Society, 2000, vol. 122, # 35, p. 8357 - 8364]

13
[ 7295-76-3 ]
[ 88070-48-8 ]
[ 75-16-1 ]
N-(3-methoxy-2-methyl-2H-pyridin-1-yl)-N-methyl-benzamidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: 3-methoxypyridine; N-methylbenzamide With trifluoromethylsulfonic anhydride In dichloromethane at -40 - 20℃; Stage #2: methylmagnesium bromide In dichloromethane at -70℃;

Reference： [1]Lemire, Alexandre; Grenon, Michel; Pourashraf, Mehrnaz; Charette, Andre B. [Organic Letters, 2004, vol. 6, # 20, p. 3517 - 3520]

14
[ 7295-76-3 ]
[ 88070-48-8 ]
phenylmagnesium bromide [ No CAS ]
N-(3-methoxy-2-phenyl-2H-pyridin-1-yl)-N-methyl-benzamidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: 3-methoxypyridine; N-methylbenzamide With trifluoromethylsulfonic anhydride In dichloromethane at -40 - 20℃; Stage #2: phenylmagnesium bromide In dichloromethane at -70℃;

Reference： [1]Lemire, Alexandre; Grenon, Michel; Pourashraf, Mehrnaz; Charette, Andre B. [Organic Letters, 2004, vol. 6, # 20, p. 3517 - 3520]

15
[ 7295-76-3 ]
[ 113118-83-5 ]

Reference： [1]Heterocycles,1987,vol. 26,p. 2159 - 2164

16
[ 7295-76-3 ]
[ 10201-71-5 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1955,vol. 74,p. 1171,1174
[2]Journal of the American Chemical Society,1947,vol. 69,p. 1147,1148

17
[ 7295-76-3 ]
[ 52334-90-4 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1955,vol. 74,p. 1160,1164
[2]Patent: CN109020957,2018,A

18
[ 7295-76-3 ]
[ 576-83-0 ]
[ 1849-53-2 ]

Yield	Reaction Conditions	Operation in experiment
	With tert.-butyl lithium; In tetrahydrofuran; N,N-dimethyl-formamide;	(a) To a solution of t-BuLi (216 ml, 1.7M, 0.367 mol) in 1 L of THF at -78 C was added dropwise 1-bromo-2,4,6-trimethyl-benzene (35.6 g, 0.178 mol) over a period of 45 minutes. The mixture was stirred at -78 C. for 1 hour, 3-methoxypyridine (15 g, 0.138 mol) was added and then the mixture was stirred at -23 C. for 3 hours. The above reaction mixture was cooled to -78 C. and 13 g (0.2 mol) of DMF in 25 ml of THF was added and the mixture was stirred for 1 hour. The reaction mixture was quenched with 250 ml of brine, the mixture was stirred overnight, and diluted with 1 L of ether. The aqueous layer was extracted with ethyl acetate (1 L), the combined organic layer was dried over potassium carbonate, and concentrated in vacuo to afford 7.5 g of 3-methoxypyridyl-2-carboxaldehyde.

Reference： [1]Patent: US5554620,1996,A

19
[ 420-12-2 ]
[ 7295-76-3 ]
1-(2-mercaptoethyl)-3-methoxypyridinium methanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76.3%	With methanesulfonic acid	10.A A. A. 1-(2-mercaptoethyl)-3-methoxypyridinium methanesulfonate STR181 To precooled (5° C.) 3-methoxypyridine (698 mg, 6.4 mmol) was added dropwise methanesulfonic acid (0.216 mL, 3.05 mmol) and ethylene sulfide (0.19 mL, 3.2 mmol). The mixture was then heated at 60° C. for 18 h, cooled to 20° C., diluted with water (10 mL) and washed with ether (3*10 mL). The aqueous phase was pumped under high vacuum for 15 min and poured on a C18 reverse phase column. The title compound was eluted with water. The appropriate fractions were combined and evaporated under high vacuum to give the desired thiol (61.6 mg, yield 76.3%); ir (CH2 Cl2) νmax:2550 (w, SH) and 1620, 1600, 1585 cm-1 (m, aromatic); 1 Hmr (DMSO d6) δ: 8.90-7.90 (4H, m, aromatic C-H), 4.72 (2H, t, J=6.6 Hz, CH2 N+), 4.01 (3H, s, OCH3), 3.5-3.0 (m, hidden CH2 S), 2.66 (1H, dd, J=9.6 Hz, J=7.5 Hz, SH) and 2.31 ppm (3H, s, CH3 SO3).

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US4552696, 1985, A

20
[ 7295-76-3 ]
[ 576-83-0 ]
[ 22924-15-8 ]
[ 594-19-4 ]
α-(3-methoxypyridin-2-yl)-3-ethoxybenzyl alcohol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With sodium chloride In tetrahydrofuran; pentane	75.A A. A. Synthesis of α-(3-methoxypyridin-2-yl)-3-ethoxybenzyl alcohol To a solution of 2-bromomesitylene (9.16 ml, 60 m mol) in tetrahydrofuran (250 ml), a 1.64 M pentane solution of tert-butyl lithium (73 ml, 120 m mol) was added dropwise at -50° C. or below. After this mixture was stirred for 30 minutes, 3-methoxypyridine (5.0 g, 46 m mol) was added dropwise thereto at -50° C. or below and the resulting mixture was stirred at -20° C. for 2 hours. After the reaction mixture was cooled again to -50° C. or below, 3-ethoxybenzaldehyde (10.3 g, 69 m mol) was added dropwise thereto and the stirring was continued for another 30 minutes. After the addition of a saturated aqueous solution of sodium chloride (10 ml), the reaction mixture was returned to room temperature. After a saturated aqueous solution of sodium chloride (200 ml) was further added thereto, the organic layer was separated. The aqueous layer was extracted with ethyl acetate (200 ml), and the extract was combined with the previous organic layer. After the combined organic layer was washed with a saturated aqueous solution of sodium chloride (50 ml) and dried over magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting solid was washed with hexane and then recrystallized from methanol (300 ml) to obtain the desired compound (7.0 g, 59%) as colorless crystals. Melting point: 104.5-106° C.; 1H-NMR (CDCl3): δ 8.17 (dd, J=4.0, 1.9, 1H), 7.30-6.60 (m, 6H), 5.92 (d, J=7.3, 1H), 5.35 (d, J=7.3, 1H), 3.99 (q, J=7.0, 2H), 3.76 (s, 3H), 1.37 (t, J=7.0, 3H).

Reference： [1]Current Patent Assignee: SUGI HOLDINGS CO., LTD. - US6291485, 2001, B1

21
[ 7295-76-3 ]
[ 75-77-4 ]
[ 118005-98-4 ]

Yield	Reaction Conditions	Operation in experiment
53%	Stage #1: 3-methoxypyridine With trimethylsilylmethyllithium In tetrahydrofuran at -20℃; for 1h; Stage #2: chloro-trimethyl-silane In tetrahydrofuran at -20 - 20℃;	4 EXAMPLE 4; Deprotonation of azaaromatic using (trimethylsilylmethyl) lithium A dry 50 mL 3-neck round bottom flask was charged with (trimethylsilylmethyl) lithium (20.9 mL, 12.7 weight percent) and cooled TO-20 °C. Tetrhydrofuran (15 mL) was added to the flask followed by the addition of 3- methoxypyridine (2. 0 g). After 1 hour, CHLOROTRIMETHYLSILANE (2.6 mL) was added to the flask. The mixture was allowed to warm to ambient temperature overnight. The mixture was concentrated in vacuo and partitioned with 5 percent NAHC03 (10 mL) and methyl tert-butyl ether (15 mL). The methyl tert-butyl ether layers were combined, dried over MGS04 and concentrated, resulting in 2.61 grams of orange liquid. The product was purified by silica gel column chromatography to afford 1.76 grams of 3-methoxy-4-trimethylsilylpyridine (53% yield). The structure of the product was confirmed by gas chromatography and mass spectroscopy (molecular weight equal to 181) AND H NMR (0.3 ppm, S, 9H); (3.9 ppm, s, 3H); (7.2 ppm, M, 1H); and (8. 2 ppm, M, 2H).

Reference： [1]Current Patent Assignee: FMC CORP - WO2004/92125, 2004, A2 Location in patent: Page 8

22
[ 7295-76-3 ]
[ 93560-55-5 ]

Yield	Reaction Conditions	Operation in experiment
50%	Stage #1: 3-methoxypyridine With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; zinc dichloro(N,N,N′,N′-tetramethylethylenediamine) In tetrahydrofuran; hexane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; hexane at 20℃; Inert atmosphere; regioselective reaction;	4.2. General procedure 1 General procedure: To a stirred, cooled (0 C) solution of 2,2,6,6-tetramethylpiperidine (0.25 mL, 1.5 mmol) in THF (2-3 mL) were successively added BuLi (about 1.6 M hexanes solution, 1.5 mmol) and, 5 min later, ZnCl2TMEDA[51] (0.13 g, 0.50 mmol). The mixture was stirred for 15 min at 0 C before introduction of the substrate (1.0 mmol) at 0-10 C. After 2 h at room temperature, a solution of I2 (0.38 g, 1.5 mmol) in THF (4 mL) was added. The mixture was stirred overnight before addition of an aqueous saturated solutionof Na2S2O3 (4 mL) and extraction with AcOEt (320 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. Purification by chromatographyon silica gel (the eluent is given in the product description) led to the compounds described below. 4.2.1. 2-Iodo-3-methoxypyridine (1b). The general procedure 1, but with a 10 min contact time between the base and the substrate instead of 2 h, using 3-methoxypyridine (0.10 mL) gave 1b (eluent: heptane-AcOEt 20:80) in 50 % yield as a yellow oil: 1H NMR (CDCl3) δ 3.86 (s, 3H), 6.97 (dd, 1H, J8.1 and 1.5 Hz), 7.17 (dd, 1H, J8.1 and 4.5 Hz), 7.95 (dd, 1H, J 4.5 and 1.5 Hz); 13C NMR (CDCl3) δ 56.4 (CH3), 111.6 (C), 116.9 (CH), 123.6 (CH), 142.5 (CH), 155.3 (C). These data are in accordance with those previously described.[52]
	With 1,10-Phenanthroline; iodine In 1,4-dioxane; m-xylene Inert atmosphere; regioselective reaction;
	With potassium phosphate; iodine; lithium tert-butoxide In 1,4-dioxane at 120℃; for 1h; Inert atmosphere;

Stage #1: 3-methoxypyridine With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; dichloro(N,N,N’,N‘-tetramethylethylenediamine)zinc In tetrahydrofuran; hexane at 20℃; for 2h; Inert atmosphere; Schlenk technique; Stage #2: With iodine In tetrahydrofuran; hexane Inert atmosphere; Schlenk technique;

2 General procedure 1 General procedure: To a stirred, cooled (0°C) solution of 2,2,6,6-tetramethylpiperidine (0.25 mL, 1.5 mmol) in THF (2-3 mL) were successively added BuLi (about 1.6 M hexanes solution, 1.5 mmol) and, 5 min later, ZnCl2*TMEDA (0.13 g, 0.50 mmol). The mixture was stirred for 15 min at 0°C before introduction of the substrate (1.0 mmol) at 0-10°C. After 2 h at room temperature, a solution of I2 (0.38 g, 1.5 mmol) in THF (4 mL) was added. The mixture was stirred overnight before addition of an aqueous saturated solution of Na2S2O3 (4 mL) and extraction with AcOEt (3x20 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. To the crude iodide were added Cs2CO3 (0.65 g, 2.0 mmol), Cu powder (13 mg, 0.20 mmol), the azole (1.5 mmol) and MeCN (5 mL) and the resulting mixture was heated under reflux for 24 h. Filtration over Celite, washing with AcOEt, removal of the solvent and purification by chromatography on silica gel (the eluent is given in the product description) led to the compound described below.

Reference： [1]Hedidi, Madani; Bentabed-Ababsa, Ghenia; Derdour, Aïcha; Halauko, Yury S.; Ivashkevich, Oleg A.; Matulis, Vadim E.; Chevallier, Floris; Roisnel, Thierry; Dorcet, Vincent; Mongin, Florence [Tetrahedron, 2016, vol. 72, # 17, p. 2196 - 2205]
[2]Do, Hien-Quang; Daugulis, Olafs [Organic Letters, 2010, vol. 12, # 11, p. 2517 - 2519]
[3]Do, Hien-Quang; Daugulis, Olafs [Journal of the American Chemical Society, 2011, vol. 133, # 34, p. 13577 - 13586]
[4]Hedidi, Madani; Erb, William; Bentabed-Ababsa, Ghenia; Chevallier, Floris; Picot, Laurent; Thiéry, Valérie; Bach, Stéphane; Ruchaud, Sandrine; Roisnel, Thierry; Dorcet, Vincent; Mongin, Florence [Tetrahedron, 2016, vol. 72, # 41, p. 6467 - 6476]

23
[ 7295-76-3 ]
[ 1942-45-6 ]
[ 1239454-17-1 ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: 3-methoxypyridine With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; N-(2-(3-mesityl-2,3-dihydro-1H-imidazol-1-yl)ethyl)-2-methylpropan-2-amine; trimethylaluminum In n-heptane; toluene for 0.0833333h; Inert atmosphere; Stage #2: 4-Octyne In n-heptane; toluene at 80℃; for 16h; Inert atmosphere; regioselective reaction;

Reference： [1]Tsai, Chung-Chih; Shih, Wei-Chih; Fang, Cyong-Hui; Li, Chia-Yi; Ong, Tiow-Gan; Yap, Glenn P. A. [Journal of the American Chemical Society, 2010, vol. 132, # 34, p. 11887 - 11889]

24
[ 7295-76-3 ]
[ 108-85-0 ]
[ 1242676-13-6 ]

Yield	Reaction Conditions	Operation in experiment
83%	With iron(III) chloride; TMPMgCl*LiCl; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane In tetrahydrofuran at 20℃; Inert atmosphere;

Reference： [1]Tran, Ly Dieu; Daugulis, Olafs [Organic Letters, 2010, vol. 12, # 19, p. 4277 - 4279]

25
[ 7295-76-3 ]
[ 137-43-9 ]
[ 1242676-23-8 ]

Yield	Reaction Conditions	Operation in experiment
81%	With iron(III) chloride; TMPMgCl*LiCl; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane In tetrahydrofuran at 20℃; Inert atmosphere;

Reference： [1]Tran, Ly Dieu; Daugulis, Olafs [Organic Letters, 2010, vol. 12, # 19, p. 4277 - 4279]

26
[ 7295-76-3 ]
[ 629-04-9 ]
[ 1242676-17-0 ]

Yield	Reaction Conditions	Operation in experiment
82%	With iron(III) chloride; TMPMgCl*LiCl; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane In tetrahydrofuran at 20℃; Inert atmosphere;

Reference： [1]Tran, Ly Dieu; Daugulis, Olafs [Organic Letters, 2010, vol. 12, # 19, p. 4277 - 4279]

27
[ 7295-76-3 ]
[ 629-27-6 ]
[ 1242676-18-1 ]

Yield	Reaction Conditions	Operation in experiment
78%	With iron(III) chloride; TMPMgCl*LiCl; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane In tetrahydrofuran at 20℃; Inert atmosphere;

Reference： [1]Tran, Ly Dieu; Daugulis, Olafs [Organic Letters, 2010, vol. 12, # 19, p. 4277 - 4279]

28
[ 7295-76-3 ]
[ 34683-73-3 ]
[ 1242676-20-5 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 4277 - 4279

29
[ 7295-76-3 ]
[ 406-81-5 ]
[ 1242676-21-6 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 4277 - 4279

30
[ 7295-76-3 ]
[ 100-39-0 ]
[ 20071-88-9 ]

Yield	Reaction Conditions	Operation in experiment
28%	With iron(III) chloride; TMPMgCl*LiCl; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane In tetrahydrofuran at 20℃; Inert atmosphere;

Reference： [1]Tran, Ly Dieu; Daugulis, Olafs [Organic Letters, 2010, vol. 12, # 19, p. 4277 - 4279]

31
[ 7295-76-3 ]
[ 1119-51-3 ]
[ 1242676-19-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With iron(III) chloride; TMPMgCl*LiCl; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane In tetrahydrofuran at 20℃; Inert atmosphere;

Reference： [1]Tran, Ly Dieu; Daugulis, Olafs [Organic Letters, 2010, vol. 12, # 19, p. 4277 - 4279]

32
[ 7295-76-3 ]
[ 7051-34-5 ]
[ 1242676-22-7 ]

Yield	Reaction Conditions	Operation in experiment
62%	With iron(III) chloride; TMPMgCl*LiCl; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane In tetrahydrofuran at 20℃; Inert atmosphere;

Reference： [1]Tran, Ly Dieu; Daugulis, Olafs [Organic Letters, 2010, vol. 12, # 19, p. 4277 - 4279]

33
[ 7295-76-3 ]
[ 108-90-7 ]
[ 53698-50-3 ]

Yield	Reaction Conditions	Operation in experiment
71%	With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran; hexane; pentane at -13℃; for 12h; Inert atmosphere; regioselective reaction;
	With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran; diethyl ether at -45℃; for 36h; Inert atmosphere; Sealed tube;
	With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran at -13℃;

Reference： [1]Truong, Thanh; Daugulis, Olafs [Journal of the American Chemical Society, 2011, vol. 133, # 12, p. 4243 - 4245]
[2]Truong, Thanh; Mesgar, Milad; Le, Ky Khac Anh; Daugulis, Olafs [Journal of the American Chemical Society, 2014, vol. 136, # 24, p. 8568 - 8576]
[3]Pang, Jia Hao; Kaga, Atsushi; Chiba, Shunsuke [Chemical Communications, 2018, vol. 54, # 73, p. 10324 - 10327]

34
[ 7295-76-3 ]
[ 185990-03-8 ]
[ 1295576-61-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With (η(3)-allyl)PdCl * tricyclohexylphosphine In toluene at 50℃; for 96h; Inert atmosphere; regioselective reaction;
95%	In toluene 50°C, 96 h;

Reference： [1]Oshima, Kazuyuki; Ohmura, Toshimichi; Suginome, Michinori [Journal of the American Chemical Society, 2011, vol. 133, # 19, p. 7324 - 7327]
[2]Oshima, Kazuyuki; Ohmura, Toshimichi; Suginome, Michinori [Journal of the American Chemical Society, 2011, vol. 133, # 19, p. 7324 - 7327]

35
[ 7295-76-3 ]
[ 1331850-50-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: 3-methoxypyridine With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; zinc dichloro(N,N,N′,N′-tetramethylethylenediamine) In tetrahydrofuran; hexane at 20℃; for 2h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; hexane at 20℃; Inert atmosphere; regioselective reaction;	4.2. General procedure 1 General procedure: To a stirred, cooled (0 C) solution of 2,2,6,6-tetramethylpiperidine (0.25 mL, 1.5 mmol) in THF (2-3 mL) were successively added BuLi (about 1.6 M hexanes solution, 1.5 mmol) and, 5 min later, ZnCl2TMEDA[51] (0.13 g, 0.50 mmol). The mixture was stirred for 15 min at 0 C before introduction of the substrate (1.0 mmol) at 0-10 C. After 2 h at room temperature, a solution of I2 (0.38 g, 1.5 mmol) in THF (4 mL) was added. The mixture was stirred overnight before addition of an aqueous saturated solutionof Na2S2O3 (4 mL) and extraction with AcOEt (320 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. Purification by chromatographyon silica gel (the eluent is given in the product description) led to the compounds described below.
70%	Stage #1: 3-methoxypyridine With (THF)Li(TMP)Zn(tBu)2 In tetrahydrofuran at 25℃; for 2h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; regioselective reaction;	Synthesis of 3-iodo-2-methoxypyridine 2a 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 2-methoxypyridine (0.042 mL, 0.4 mmol) was added and the resultant light orange reaction allowed to stir at room temperature for 2 hours. Next the solution was cooled to 0°C and quenched with I2 (508 mg, in 1 mL THF) and allowed to stir for 1 hour. Next a 10% 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 Heptane:DCM as eluent (20:80-->40:60) to give 3-iodo2-methoxypyridine 2a as a colourless oil (87.1 mg, 92% yield).
58%	Stage #1: 3-methoxypyridine With (PMDETA)<SUB>2</SUB>K<SUB>2</SUB>Mg(CH<SUB>2</SUB>SiMe<SUB>3</SUB>)<SUB>4</SUB> at 0℃; for 2h; Inert atmosphere; Schlenk technique; Stage #2: With iodine for 1h; Inert atmosphere; Schlenk technique; regioselective reaction;

19%

Stage #1: 3-methoxypyridine With 2,2,6,6-tetramethylpiperidinyl-lithium; tert.-butyl lithium; zinc(II) chloride In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran at 0℃; for 1h;

1.3 1.3 Preparation of A16 1.3 Preparation of A16 ZnCl2 (540 mg, 4 mmol) was dissolved in THF (10 mL) and cooled to -78° C. under N2 atmosphere. t-BuLi (5.6 mL, 8 mmol) was added dropwise and the solution was allowed to stir at -78° C. for 40 min. In a separated vial containing TMPH (4 mmol) and THF (10 mL), n-BuLi (4 mmol) was added dropwise at -78° C. and the solution was allowed to stir for 40 min reaching rt. Then LiTMP solution was introduced to the in situ t-Bu2Zn solution at -78° C., stirred for 30 min and warmed gradually to 0° C. Compound 1 (436 mg, 4 mmol) was added and the resulting mixture stirred at rt for 2 h. Then the mixture was cooled to 0° C. and I2 (1 g, 4 mmol) in THF (10 mL) was added and stirred for 1 h. A 10% solution of Na2S2O3 was added and the mixture was extracted with EA. The organic layer was dried and concentrated to give the crude product, and purified by column to give the product, A1. (185 mg, yield: 19%). LCMS: 236 [M+1].

Reference： [1]Hedidi, Madani; Bentabed-Ababsa, Ghenia; Derdour, Aïcha; Halauko, Yury S.; Ivashkevich, Oleg A.; Matulis, Vadim E.; Chevallier, Floris; Roisnel, Thierry; Dorcet, Vincent; Mongin, Florence [Tetrahedron, 2016, vol. 72, # 17, p. 2196 - 2205]
[2]Blair, Victoria L.; Blakemore, David C.; Hay, Duncan; Hevia, Eva; Pryde, David C. [Tetrahedron Letters, 2011, vol. 52, # 36, p. 4590 - 4594]
[3]Baillie, Sharon E.; Bluemke, Tobias D.; Clegg, William; Kennedy, Alan R.; Klett, Jan; Russo, Luca; De Tullio, Marco; Hevia, Eva [Chemical Communications, 2014, vol. 50, # 85, p. 12859 - 12862]
[4]Current Patent Assignee: JOHNSON & JOHNSON INC - US2015/132258, 2015, A1 Location in patent: Paragraph 0337; 0338

36
[ 7295-76-3 ]
[ 106-39-8 ]
[ 1331850-61-3 ]

Yield	Reaction Conditions	Operation in experiment
30%	Stage #1: 3-methoxypyridine With (THF)Li(TMP)Zn(tBu)2 In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Stage #2: bromochlorobenzene With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran at 100℃; for 0.166667h; Inert atmosphere; Microwave irradiation;	Synthesis of 4-(4-chlorophenyl)-3-methoxypyridine 3b 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 3-methoxypyridine (0.042 mL, 0.4 mmol) was added and the resultant light orange reaction allowed to stir at room temperature for 2 hours. This solution was then transferred to a THF (1 mL) solution of PdCl2(dppf) (29.3 mg, 10 mol %) and 1-bromo-4-chlorobenzene (76.6 mg, 0.4 mmol) to give a heterogeneous red solution. The reaction mixture was then reacted in the microwave at 100°C for 10 minutes. The reaction was then quenched with saturated NH4Cl solution (2 mL) and extracted with DCM (3 x 1 mL). The organic fractions were combined and dried by passing through a phase separator cartridge with a hydrophobic frit and the solvent removed under reduced pressure. The residue was purified by column chromatography using a 4 g C18 silica cartridge and eluent Acetonitrile + 0.1 % formic acid:H2O + 0.1 % formic acid (5:95 to 95:5) to give compound 3b as an off white solid 26.5 mg (30% yield) 1H NMR (400 MHz, CDCl3) δ ppm 3.93 (s, 3H) 7.24 (d, J=4.69 Hz, 1 H) 7.39 - 7.46 (m, 2 H) 7.48 - 7.56 (m, 2 H) 8.33 (d, J=4.49 Hz, 1 H) 8.39 (s, 1 H).

Reference： [1]Blair, Victoria L.; Blakemore, David C.; Hay, Duncan; Hevia, Eva; Pryde, David C. [Tetrahedron Letters, 2011, vol. 52, # 36, p. 4590 - 4594]

37
[ 626-55-1 ]
[ 67-56-1 ]
[ 7295-76-3 ]

Yield	Reaction Conditions	Operation in experiment
78%	With 5-(di(adamantan-1-yl)phosphino)-1′,3′,5′-triphenyl-1′H-1,4′-bipyrazole; palladium diacetate; caesium carbonate In toluene at 80℃; for 24h;
74%	With sodium hydroxide at 40℃; for 14h; Inert atmosphere; Irradiation;
55%	With triethylamine at 20℃; for 72h; Irradiation; Schlenk technique;

Reference： [1]Gowrisankar, Saravanan; Neumann, Helfried; Beller, Matthias [Chemistry - A European Journal, 2012, vol. 18, # 9, p. 2498 - 2502]
[2]Vijeta, Arjun; Casadevall, Carla; Roy, Souvik; Reisner, Erwin [Angewandte Chemie - International Edition, 2021, vol. 60, # 15, p. 8494 - 8499][Angew. Chem., 2021, vol. 133, # 15, p. 8575 - 8580,6]
[3]Chen, Hao; Dong, Wenbo; Hu, Jianxiang; Rao, Li; Wang, Pei; Wang, Shengyao; Xiang, Yonggang; Yang, Yi [Green Chemistry, 2021, vol. 23, # 16, p. 5797 - 5805]

38
[ 7295-76-3 ]
[ 25015-63-8 ]
[ 1360145-64-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; tricyclohexylphosphine In toluene at 50℃; for 24h; Inert atmosphere; regioselective reaction;
91%	With P(C₆H₁₁)3 In toluene ligand reacted with pinacolborane in toluene at 50°C for 24 h in presence of (Rh(C8H12)Cl)2 and P(C6H11)3; treated with activated charcoal, filtered under N2, concd. in vacuo;
91%	With [((2,6-ⁱPr₂-C₆H₃)NC(Me)CHP(Cy₂)N(2,6-Me₂-C₆H₃))MgH]₂; methyltriphenylsilane In benzene-d6 at 25℃; regioselective reaction;

80%	With [La(η5-C5(CH3)5)H]2 at 25 - 35℃; for 21h;
80%	With C₂₈H₂₉NiOP In benzene-d6 at 30℃; for 12h; regioselective reaction;
80 %Spectr.	With [La(η5-C5(CH3)5)H]2 In Cyclohexane-d12 at 35℃; for 21h; regiospecific reaction;
61 %Spectr.	With [Cp*(Ph₂PC₆H₄S)Fe]₂(μ-N₂) In benzene-d6 at 50℃; for 24h; Inert atmosphere; regioselective reaction;
67 %Spectr.	With {Cp'2Th(μ-H)H}2 In benzene-d6 at 70℃; for 24h; regioselective reaction;

Reference： [1]Oshima, Kazuyuki; Ohmura, Toshimichi; Suginome, Michinori [Journal of the American Chemical Society, 2012, vol. 134, # 8, p. 3699 - 3702]
[2]Oshima, Kazuyuki; Ohmura, Toshimichi; Suginome, Michinori [Journal of the American Chemical Society, 2012, vol. 134, # 8, p. 3699 - 3702]
[3]Liu, Xinli; Li, Bingwen; Hua, Xiufang; Cui, Dongmei [Organic Letters, 2020, vol. 22, # 13, p. 4960 - 4965]
[4]Current Patent Assignee: NORTHWESTERN UNIVERSITY (ILLINOIS) - US2016/159825, 2016, A1 Location in patent: Paragraph 0062
[5]Liu, Jianguo; Chen, Jia-Yi; Jia, Mengjing; Ming, Bangrong; Jia, Jiong; Liao, Rong-Zhen; Tung, Chen-Ho; Wang, Wenguang [ACS Catalysis, 2019, vol. 9, # 5, p. 3849 - 3857]
[6]Dudnik, Alexander S.; Weidner, Victoria L.; Motta, Alessandro; Delferro, Massimiliano; Marks, Tobin J. [Nature Chemistry, 2014, vol. 6, # 12, p. 1100 - 1107]
[7]Zhang, Fanjun; Song, Heng; Zhuang, Xuewen; Tung, Chen-Ho; Wang, Wenguang [Journal of the American Chemical Society, 2017, vol. 139, # 49, p. 17775 - 17778]
[8]Liu, Heng; Khononov, Maxim; Eisen, Moris S. [ACS Catalysis, 2018, vol. 8, # 4, p. 3673 - 3677]

39
[ 7295-76-3 ]
[ 630-19-3 ]
[ 1369964-31-7 ]

Yield	Reaction Conditions	Operation in experiment
5%	Stage #1: 3-methoxypyridine With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; iron(II) bromide In tetrahydrofuran; hexane at 0 - 20℃; for 2h; Stage #2: pivalaldehyde In tetrahydrofuran; hexane at 20℃; for 1h;	4.2. General procedure B (deprotonation using 1 equiv FeBr₂ and 3 equiv LiTMP followed by trapping with an electrophile≠I₂) General procedure: To a stirred cooled (0 °C) solution of 2,2,6,6-tetramethylpiperidine (1.0 mL, 6.0 mmol) in THF (5 mL) were added BuLi (1.6 M hexanes solution, 6.0 mmol) and, 5 min later, FeBr2 (0.43 g, 2.0 mmol). The mixture was stirred for 15 min at 0 °C before introduction of the substrate (2.0 mmol). After 2 h at room temperature, the electrophile (6.0 mmol) was added. The mixture was stirred for 1 h before addition of H2O (10 mL) and extraction with EtOAc (3×20 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure.

Reference： [1]Location in patent: experimental part Nagaradja, Elisabeth; Chevallier, Floris; Roisnel, Thierry; Jouikov, Viatcheslav; Mongin, Florence [Tetrahedron, 2012, vol. 68, # 14, p. 3063 - 3073]

40
[ 110-91-8 ]
[ 7295-76-3 ]
[ 92670-29-6 ]

Yield	Reaction Conditions	Operation in experiment
61%	With bis(1,5-cyclooctadiene)nickel⁽⁰⁾; sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In toluene at 100℃; for 12h; Inert atmosphere; Sealed vessel;	III. Typical Procedure for Ni-Catalyzed Amination of N-Heteroaryl Methyl Ethers (Entry 1 in Table 2) General procedure: Ni(cod)2(27.5 mg, 0.1 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (85.0 mg, 0.2 mmol), sodium tert-butoxide (288.3 mg, 3.0 mmol), 6-methoxyquinoline (1,79.6 mg, 0.5 mmol), morpholine (2, 217.8 mg, 2.5 mmol) and toluene (1.5 mL) were added to a 10 mL sample vial with a Teflon-sealed screwcap in a glovebox filled withnitrogen. After the cap was closed, the vial was stirred at 100 °C for 12 h. After cooling to room temperature, the crude mixture was filtered through a Celite pad. The filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (hexane/EtOAc = 1:1) to give 4-(quinolin-6-yl)morpholine (3, 58.9 mg, 74 %) as a white solid.

Reference： [1]Tobisu, Mamoru; Yasutome, Ayaka; Yamakawa, Ken; Shimasaki, Toshiaki; Chatani, Naoto [Tetrahedron, 2012, vol. 68, # 26, p. 5157 - 5161]

41
[ 7295-76-3 ]
[ 1402599-34-1 ]
[ 1402598-23-5 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-methoxypyridine With 2,4,6-trimethylphenyl bromide; tert.-butyl lithium In tetrahydrofuran; pentane at -78 - -23℃; Stage #2: N-(1-benzothiophen-2-ylmethylidene)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide In tetrahydrofuran; pentane at 0℃; for 0.583333h; Stage #3: With methanol In tetrahydrofuran; pentane	43 A 25 mL round-bottomed flask was charged with 2-bromo-l,3,5- trimethylbenzene (0.53 g, 2.7 mmol, Sigma-Aldrich, St. Louis, MO) and tetrahydrofuran (5.6 mL). The solution was cooled to -78 °C, t-butyllithium (3.4 mL of a 1.7 M solution with pentane, 5.4 mmol, Sigma-Aldrich, St. Louis, MO) was added, and then the reaction mixture was stirred for 1 h. After that time, the reaction mixture was warmed to -23 °C, 3-methoxypyridine (0.29 g, 2.7 mmol, Sigma-Aldrich, St. Louis, MO) was added, and then the reaction mixture was stirred for 3 h. After that time, an aliquot of this reaction mixture (1.0 mL) was added to a solution of N-(l-benzothiophen-2-ylmethylidene)-3,4-dihydro-2H-l,5- benzodioxepine-7-sulfonamide (intermediate B)(0.10 g, 0.27 mmol) and tetrahydrofuran (2.8 mL) at 0 °C. After stirring for 35 min, methanol (1.0 mL) and silica gel (0.50 g) were added sequentially and the volatiles were removed under a vacuum. The residue was subjected to flash chromatography on silica gel (6.5 g of silica gel, gradient elution with 6: 1 to 2: 1 hexane-ethyl acetate), and then the isolated material was re-subjected to flash chromatography on silica gel (3.0 g of silica gel, 99.5:0.5 dichloromethane -methanol) to give N-(l-benzothiophen-2- yl(3-methoxy-2-pyridinyl)methyl)-3,4-dihydro-2H-l,5-benzodioxepine-7- sulfonamide (0.024 g) as a pale yellow tar (racemic mixture).1H NMR (400 MHz, chloroform-d) δ 8.09 (d, J= 4.7 Hz, 1 H), 7.65 (d, J = 7.8 Hz, 1 H), 7.59 (d, J= 7.4 Hz, 1 H), 7.32 - 7.17 (m, 4 H), 7.15 (dd, J= 4.7, 8.2 Hz, 1 H), 7.07 (d, J= 8.2 Hz, 1 H), 7.03 (s, 1 H), 6.79 - 6.67 (m, 2 H), 6.30 (d, J = 9.0 Hz, 1 H), 4.15 - 3.95 (m, 3 H), 3.89 (m, 1 H), 3.80 (s, 3 H), 2.17 - 2.00 (m, 2 H). m/z (ESI, +ve ion) 482.9 (M+H)+. GK-GKRP EC50 (LCMS/MS) = 0.047 μΜ. GK-GKRP IC50 (Binding) = 0.041 μΜ.

Reference： [1]Current Patent Assignee: AMGEN INC - WO2012/138776, 2012, A1 Location in patent: Page/Page column 139-140

42
[ 7295-76-3 ]
[ 1402599-37-4 ]
[ 1402598-30-4 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-methoxypyridine With 2,4,6-trimethylphenyl bromide; tert.-butyl lithium In tetrahydrofuran; pentane at -78 - -23℃; Stage #2: N-(thieno[2,3-b]pyridin-2-ylmethylidene)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide In tetrahydrofuran; pentane for 0.666667h; Stage #3: With methanol In tetrahydrofuran; pentane	50 A 25 mL round-bottomed flask was charged with tetrahydrofuran (12 mL) and t-butyllithium (4.2 mL of a 1.7 M solution with pentane, 7.1 mmol, Sigma- Aldrich, St. Louis, MO) at -78 °C, 2-bromo-l,3,5-trimethylbenzene (0.70 g, 3.5 mmol, Sigma- Aldrich, St. Louis, MO) was added, and then the reaction mixture was stirred for 30 min. After that time, 3-methoxypyridine (0.39 g, 3.5 mmol, Sigma- Aldrich, St. Louis, MO) was added, and then the reaction mixture was warmed to -23 °C. After stirring for 3 h, an aliquot of this reaction mixture (1.0 mL) was added to a solution of N-(thieno[2,3-b]pyridin-2-ylmethylidene)-3,4- dihydro-2H-l,5-benzodioxepine-7-sulfonamide (intermediate D)(0.44 g, 1.2 mmol) and tetrahydrofuran (12 mL). After stirring for 40 min, methanol (1.0 mL) and silica gel (0.50 g) were added sequentially and the volatiles were removed under a vacuum. The residue was subjected to flash chromatography on silica gel (28 g of silica gel, 49: 1 dichloromethane-methanol), and then the isolated material was re-subjected to flash chromatography on silica gel (4.0 g of silica gel, 49: 1 dichloromethane-methanol) to give N-((3-methoxy-4-pyridinyl)(thieno[2,3- b]pyridin-2-yl)methyl)-3,4-dihydro-2H-l,5-benzodioxepine-7-sulfonamide (0.043 g) as a pale yellow solid (racemic mixture).1H NMR (400 MHz, DMSO-d6) δ 9.10 (br. s., 1 H), 8.48 (dd, J= 1.6, 4.5 Hz, 1 H), 8.28 (s, 1 H), 8.14 - 8.05 (m, 2 H), 7.41 - 7.29 (m, 2 H), 7.19 (dd, J = 2.2, 8.3 Hz, 1 H), 7.06 (d, J= 2.3 Hz, 1 H), 6.92 - 6.83 (m, 2 H), 6.08 (br. s., 1 H), 4.11 (t, J = 5.6 Hz, 2 H), 4.04 (t, J= 5.8 Hz, 2 H), 3.86 (s, 3 H), 2.09 (quin, J = Hz, 2 H). m/z (ESI, +ve ion) 483.8 (M+H)+. GK-GKRP EC50 (LCMS/MS) = 0, μΜ. GK-GKRP IC50 (Binding) = 0.41 μΜ.

Reference： [1]Current Patent Assignee: AMGEN INC - WO2012/138776, 2012, A1 Location in patent: Page/Page column 148-149

43
[ 7295-76-3 ]
[ 1402599-23-8 ]
[ 1402598-01-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-methoxypyridine With 2,4,6-trimethylphenyl bromide; tert.-butyl lithium In tetrahydrofuran; pentane at -78 - -23℃; Stage #2: N-(1-benzofuran-2-ylmethylidene)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide In tetrahydrofuran; pentane at 0℃; for 1.25h; Stage #3: With methanol In tetrahydrofuran; pentane	30 A 25 mL round-bottomed flask was charged with 2-bromo-l,3,5- trimethylbenzene (0.56 g, 2.8 mmol, Sigma-Aldrich, St. Louis, MO) and tetrahydrofuran (5.6 mL). The solution was cooled to -78 °C, t-butyllithium (3.5 mL of a 1.7 M solution with pentane, 5.6 mmol, Sigma-Aldrich, St. Louis, MO) was added, and then the reaction mixture was stirred for 1 h. After that time, the reaction mixture was warmed to -23 °C, 3-methoxypyridine (0.31 g, 2.8 mmol, Sigma-Aldrich, St. Louis, MO) was added, and then the reaction mixture was stirred for 3 h. After that time, an aliquot of this reaction mixture (1.0 mL) was added to a solution of N-(l-benzofuran-2-ylmethylidene)-3,4-dihydro-2H-l,5- benzodioxepine-7-sulfonamide (intermediate A)(0.10 g, 0.28 mmol) in tetrahydrofuran (2.8 mL) at 0 °C. After stirring for 75 min, methanol (1.0 mL) and silica gel (0.50 g) were added sequentially and the volatiles were removed under a vacuum. The residue was subjected to flash chromatography on silica gel (6.5 g of silica gel, gradient elution 6: 1 to 2: 1 hexane-ethyl acetate), and then the isolated material was re-subjected to flash chromatography on silica gel (3.0 g of silica gel, 99.5:0.5 dichloromethane -methanol) to give N-(l-benzofuran-2-yl(3-methoxy-2- pyridinyl)methyl)-3,4-dihydro-2H-l,5-benzodioxepine-7-sulfonamide (0.020 g) as a pale yellow tar (racemic mixture).1H NMR (400 MHz, chloroform-d) δ 8.16 - 8.08 (m, 1 H), 7.44 - 7.38 (m, 1 H), 7.32 - 7.22 (m, 3 H), 7.20 - 7.05 (m, 4 H), 6.77 - 6.63 (m, 2 H), 6.44 (s, 1 H),6.19 (d, J= 8.8 Hz, 1 H), 4.14 - 3.96 (m, 3 H), 3.96 - 3.87 (m, 1 H), 3.79 (s, 3 H),2.20 - 1.94 (m, 2 H). m/z (ESI, +ve ion) 466.9 (M+H)+. GK-GKRP EC50 (LCMS/MS) = 0.15 μΜ. GK-GKRP IC50 (Binding) = 0.31 μΜ.

Reference： [1]Current Patent Assignee: AMGEN INC - WO2012/138776, 2012, A1 Location in patent: Page/Page column 118-119

44
[ 100-42-5 ]
[ 7295-76-3 ]
3-methoxy-4-(1-phenylethyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With triethyl borane; lithium triethylborohydride; cobalt(II) bromide In tetrahydrofuran; toluene at 70℃; for 20h; Glovebox; Inert atmosphere; regioselective reaction;
85%	With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; trimethylaluminum; [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene In toluene at 130℃; for 18h; Sealed tube; regioselective reaction;
78%	Stage #1: 3-methoxypyridine With [2,2]bipyridinyl; chromium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; cyclohexylmagnesium bromide In tetrahydrofuran at 0℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: styrene In tetrahydrofuran at 80℃; for 48h; Schlenk technique; Inert atmosphere; regioselective reaction;

67 %Spectr.

With triethyl borane; sodium triethylborohydride In tetrahydrofuran at 100℃; for 12h; Inert atmosphere; regioselective reaction;

Reference： [1]Andou, Takashi; Saga, Yutaka; Komai, Hirotomo; Matsunaga, Shigeki; Kanai, Motomu [Angewandte Chemie - International Edition, 2013, vol. 52, # 11, p. 3213 - 3216][Angew. Chem., 2013, vol. 125, # 11, p. 3295 - 3298,4]
[2]Lee, Wei-Chih; Chen, Chien-Hung; Liu, Cheng-Yuan; Yu, Ming-Shiuan; Lin, Yung-Huei; Ong, Tiow-Gan [Chemical Communications, 2015, vol. 51, # 96, p. 17104 - 17107]
[3]Li, Yuexuan; Deng, Gongda; Zeng, Xiaoming [Organometallics, 2016, vol. 35, # 5, p. 747 - 750]
[4]Guan, Wei; Li, Runhan; Li, Xiaohong; Li, Yanfei; Wang, Ying; Xiong, Tao; Yin, Jianjun; Zhang, Ge; Zhang, Qian [Chemical Science, 2020, vol. 11, # 42, p. 11554 - 11561]

45
[ 7295-76-3 ]
[ 1746-23-2 ]
[ 1355203-73-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	With triethyl borane; lithium triethylborohydride; cobalt(II) bromide In tetrahydrofuran; toluene at 70℃; for 20h; Glovebox; Inert atmosphere; regioselective reaction;
61%	Stage #1: 3-methoxypyridine With [2,2]bipyridinyl; chromium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; cyclohexylmagnesium bromide In tetrahydrofuran at 0℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: 4-tert-Butylstyrene In tetrahydrofuran at 80℃; for 48h; Schlenk technique; Inert atmosphere; regioselective reaction;

Reference： [1]Andou, Takashi; Saga, Yutaka; Komai, Hirotomo; Matsunaga, Shigeki; Kanai, Motomu [Angewandte Chemie - International Edition, 2013, vol. 52, # 11, p. 3213 - 3216][Angew. Chem., 2013, vol. 125, # 11, p. 3295 - 3298,4]
[2]Li, Yuexuan; Deng, Gongda; Zeng, Xiaoming [Organometallics, 2016, vol. 35, # 5, p. 747 - 750]

46
[ 7295-76-3 ]
[ 622-97-9 ]
3-methoxy-4-(1-(p-tolyl)ethyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With triethyl borane; lithium triethylborohydride; cobalt(II) bromide In tetrahydrofuran; toluene at 70℃; for 20h; Glovebox; Inert atmosphere; regioselective reaction;
72%	Stage #1: 3-methoxypyridine With [2,2]bipyridinyl; chromium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; cyclohexylmagnesium bromide In tetrahydrofuran at 0℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: 1-ethenyl-4-methylbenzene In tetrahydrofuran at 80℃; for 48h; Schlenk technique; Inert atmosphere; regioselective reaction;

Reference： [1]Andou, Takashi; Saga, Yutaka; Komai, Hirotomo; Matsunaga, Shigeki; Kanai, Motomu [Angewandte Chemie - International Edition, 2013, vol. 52, # 11, p. 3213 - 3216][Angew. Chem., 2013, vol. 125, # 11, p. 3295 - 3298,4]
[2]Li, Yuexuan; Deng, Gongda; Zeng, Xiaoming [Organometallics, 2016, vol. 35, # 5, p. 747 - 750]

47
[ 7295-76-3 ]
[ 1331850-50-0 ]
2,4-diiodo-3-methoxypyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 61% 2: 29%	Stage #1: 3-methoxypyridine With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; dichloro(N,N,N’,N‘-tetramethylethylenediamine)zinc In tetrahydrofuran; hexane at 20℃; for 2h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; hexane Inert atmosphere; regioselective reaction;
1: 58% 2: 35%	Stage #1: 3-methoxypyridine With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; zinc dichloro(N,N,N′,N′-tetramethylethylenediamine) In tetrahydrofuran; hexane at 20℃; for 2h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; hexane at 20℃; Inert atmosphere; regioselective reaction;
1: 55% 2: 45%	Stage #1: 3-methoxypyridine With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; zinc dichloro(N,N,N′,N′-tetramethylethylenediamine) In tetrahydrofuran; hexane at 20℃; for 20h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; hexane at 20℃; Inert atmosphere; regioselective reaction;

Reference： [1]Kadiyala, Raghu Ram; Tilly, David; Nagaradja, Elisabeth; Roisnel, Thierry; Matulis, Vadim E.; Ivashkevich, Oleg A.; Halauko, Yury S.; Chevallier, Floris; Gros, Philippe C.; Mongin, Florence [Chemistry - A European Journal, 2013, vol. 19, # 24, p. 7944 - 7960]
[2]Hedidi, Madani; Bentabed-Ababsa, Ghenia; Derdour, Aïcha; Halauko, Yury S.; Ivashkevich, Oleg A.; Matulis, Vadim E.; Chevallier, Floris; Roisnel, Thierry; Dorcet, Vincent; Mongin, Florence [Tetrahedron, 2016, vol. 72, # 17, p. 2196 - 2205]
[3]Hedidi, Madani; Bentabed-Ababsa, Ghenia; Derdour, Aïcha; Halauko, Yury S.; Ivashkevich, Oleg A.; Matulis, Vadim E.; Chevallier, Floris; Roisnel, Thierry; Dorcet, Vincent; Mongin, Florence [Tetrahedron, 2016, vol. 72, # 17, p. 2196 - 2205]

48
Grubbs catalyst first generation [ No CAS ]
[ 7295-76-3 ]
C₃₇H₅₃Cl₂N₂O₂PRu^(2-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	In toluene at 20℃; for 0.166667h; Schlenk technique;	1 2.3 Synthesis of [(PCy₃)(3-MeOPy)₂(Cl)₂Ru=CHPh] A Schlenk flask was charged with (PCy3)2Cl2Ru=CHPh (1; 0.103 g, 0.125 mmol) and toluene (1 mL). 3-MeOPy (520 μL, 4.9 mmol) was added by syringe. The mixture was stirred at room temperature for 10 min and a colour change from purple to light green was observed. Pentane (15 mL) was added and a precipitate began to form. The vial was stored in a freezer -25 °C for overnight. The resulting light green precipitate was isolated, washed with cold pentane, and dried under vacuum. The green solid was collected in 72% yield. 1H NMR (500 MHz, CD2Cl2): δ 20.00 (d, JHP = 11.9 Hz, 1H, CHPh), 8.61 (s, 1H, Py), 8.48 (s, 1H, Py), 8.08 (s, 2H, Py), 8.00 (d, JHH = 7.4 Hz, 2H, ortho CH), 7.59 (t, JHH = 6.9 Hz, 1H, para CH), 7.23 (m, 2H, meta CH), 7.14 (s, 2H, Py), 7.03 (s, 2H, Py), 3.87 (s, 3H, OCH3), 3.64 (s, 3H, OCH3), 2.42-1.00 (m, 33H, PCy3); 13C NMR (126 MHz, CD2Cl2): δ 312.5 (Ru=C), 155.3 (Py: N-CH-C-O), 153.4 (ipso-C of C6H5), 139.8 (Py: N-CH-CH), 138.0 (Py: N-CH-C-O), 130.0, 128.8, 128.1 (o-, m, and p-C of C6H5), 124.6 (Py: N-CH-CH), 123.2 (Py: N-CH-CH-CH), 56.0 (OCH3), 35.3 (ipso-C of PCy3), 30.2 (m-C of PCy3), 28.2 (o-C of PCy3), 26.8 (p-C of PCy3). 31P NMR (202 MHz, acetone-d6): δ 33.98 (s, PCy3). Anal. calcd. for C37H53N2Cl2O2PRu: C 58.41, H 7.02, N 3.68; found C 58.75, H 7.44, N 3.61.

Reference： [1]Çetinkaya, Sevil; Yaşar, Emine [Applied Catalysis A: General, 2013, vol. 464-465, p. 136 - 141]

49
[ 7295-76-3 ]
[ 38202-27-6 ]
[ 81211-83-8 ]

Yield	Reaction Conditions	Operation in experiment
5.83 g	Stage #1: ethyl O-(2-mesitylenesulfonyl)acetohydroxamate With perchloric acid In 1,4-dioxane for 0.5h; Inert atmosphere; Cooling with ice; Stage #2: 3-methoxypyridine In dichloromethane at 20℃; Cooling with ice;	1 1-Amino-3-methoxypyridinium 2,4,6-trimethylbenzene sulfonate 1-Amino-3-methoxypyridinium 2,4,6-trimethylbenzene sulfonate A 70% perchloric acid aqueous solution (2.28 mL) was added to a 1,4-dioxane solution (5.5 mL) of ethyl O-mesitylsulfonylacetohydroxamate (6.28 g) under an argon atmosphere under ice-cooling, and then the mixture was stirred for 30 minutes under ice-cooling. Ice water (60 mL) was added to the reaction solution, the precipitated solid was filtered off, the obtained solid was dissolved in dichloromethane (18.5 mL), and the solution was divided into layers. The organic layer was dried over anhydrous magnesium sulfate and filtered off. A dichloromethane solution (18.5 mL) of 3-methoxypyridine (2.00 g) was added to the obtained filtrate under ice-cooling, the mixture was stirred at room temperature for 1 hour, and the reaction solution was evaporated to obtain a title compound as a colorless crystal (5.83 g). 1H-NMR (400 MHz, DMSO-d6) δ 2.17 (3H, s), 2.49 (6H, s), 3.96 (3H, s), 6.74 (2H, s), 7.90-7.93 (2H, m), 8.38-8.43 (1H, m), 8.43-8.50 (2H, brs), 8.57-8.60 (1H, m).

Reference： [1]Current Patent Assignee: KISSEI PHARMACEUTICAL COMPANY LIMITED; KYORIN HOLDINGS, INC. - EP2669285, 2013, A1 Location in patent: Paragraph 0185; 0186

50
[ 7295-76-3 ]
[ 141032-72-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 18 h / 20 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 17 h / 20 °C 3: hydrogen bromide / 16 h / Reflux
	Multi-step reaction with 3 steps 1.1: acetonitrile / 16 h / 40 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 0 °C 2.2: 16 h / 20 °C 3.1: hydrogen bromide / water / 16 h / 120 °C

Reference： [1]Möller, Dorothee; Kling, Ralf C.; Skultety, Marika; Leuner, Kristina; Hübner, Harald; Gmeiner, Peter [Journal of Medicinal Chemistry, 2014, vol. 57, # 11, p. 4861 - 4875]
[2]Current Patent Assignee: MERCK & CO INC; WUXI APPTEC CO., LTD. - WO2016/101119, 2016, A1

51
[ 7295-76-3 ]
[ 1889-58-3 ]
C₁₀H₁₇NO₄P⁽¹⁺⁾*C₆H₅S^(1-) [ No CAS ]

Reference： [1]Bulletin of the Korean Chemical Society,2014,vol. 35,p. 1329 - 1332

52
[ 7295-76-3 ]
[ 163234-74-0 ]

Reference： [1]Science,2013,vol. 342,p. 956 - 960

53
[ 7295-76-3 ]
[ 93560-55-5 ]
[ 1331850-50-0 ]
2,4-diiodo-3-methoxypyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 85% 2: 30% 3: 11%	Stage #1: 3-methoxypyridine With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; zinc dichloro(N,N,N′,N′-tetramethylethylenediamine) In tetrahydrofuran; hexane at 20℃; for 2h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; hexane at 20℃; Inert atmosphere; regioselective reaction;

54
[ 7295-76-3 ]
[ 60100-09-6 ]
5-methoxypicolinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With dipotassium peroxodisulfate; oxygen; sodium formate; silver nitrate In water at 80℃; for 4h; Schlenk technique; regioselective reaction;	general procedure for Ag-catalyzed carbamoylation General procedure: A 25 mL Schlenk flask was charged with AgNO3 (17.2 mg, 20 mol% Ag), K2S2O8(408 mg, 1.5 mmol), and HCOONa (129 mg, 1.0 mmol) before standard cycles of evacuation and back-filling with dry and pure oxygen (three times). Corresponding pyridine 1 (0.5 mmol), formamide 2 (2 mL), and H2O (0.4 mL) were added successively. The mixture was stirred at 80 °C for the indicated time (monitored byTLC). At the end of the reaction, the reaction mixture was cooled to room temperature, poured into a saturated aqueous NaCl solution (15 mL), and extracted with ethyl acetate (3 × 15 mL). The organic phases were combined, and the volatile components were evaporated in a rotary evaporator. The residue was purified by flash column chromatography on silica gel to afford the corresponding product 3
89%	With dipotassium peroxodisulfate; oxygen; sodium acetate; silver nitrate In water at 80℃; for 4h; Green chemistry;	10 Example 10 Compound 10: Under oxygen atmosphere, to a 25 ml reaction flask are sequentially added silver nitrate (0.1mmol), 3-methoxypyridine (0.5mmol), sodium acetate (1.0mmol), potassium persulphate (1.5mmol), formamide (2.0 ml) and water (0.4 ml). The mixture at 80 °C reacts for 4h. Cooling to room temperature, reducing pressure and evaporating the solvent column chromatography separation to obtain the product, yield 89%.

Reference： [1]Han, Wei; Jin, Fengli; Zhao, Qian; Du, Hongyan; Yao, Lifang [Synlett, 2016, vol. 27, # 12, p. 1854 - 1859]
[2]Current Patent Assignee: NANJING UNIVERSITY - CN105669542, 2016, A Location in patent: Paragraph 0056; 0057; 0058

55
[ 7295-76-3 ]
[ 25015-63-8 ]
3-methoxy-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,4-dihydropyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With (p-cymene)RuCl₂(PCy₃) In dichloromethane at 50℃; for 7h; Inert atmosphere; regioselective reaction;
> 99 %Spectr.	With PhC(NtBu)<SUB>2</SUB>Si(N(2,6-iPr<SUB>2</SUB>C<SUB>6</SUB>H<SUB>3</SUB>))<SUB>2</SUB>GeCF<SUB>3</SUB>SO<SUB>3</SUB> In [D₃]acetonitrile at 25℃; for 1h; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;

Reference： [1]Kaithal, Akash; Chatterjee, Basujit; Gunanathan, Chidambaram [Organic Letters, 2016, vol. 18, # 14, p. 3402 - 3405]
[2]Hu, Chaopeng; Zhang, Jianying; Yang, Hao; Guo, Lulu; Cui, Chunming [Inorganic Chemistry, 2021, vol. 60, # 18, p. 14038 - 14046]

56
[ 7295-76-3 ]
[ 909717-95-9 ]

Reference： [1]Patent: WO2016/101119,2016,A1

57
[ 7295-76-3 ]
[ 17508-17-7 ]
C₆H₃N₂O₅^(1-)*C₆H₁₁N₂O⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.50 mg	In acetonitrile at 40℃; for 16h;	90.1 Step 1: (2,4dinitrophenoxy)(3.-methoxypyridin.- I ium.- I yl)amide (49) A mixture of 3-methoxypyridine (500 mg, 4.6 mmol) and O-(2,4--dinitrophenyl)hydroxyl- amine (915 mg, 4.6 mmol) in MeCN (20 mL) was stirred at 40°C for 16 hours. After cooling to RT, the mixture was concentrated in vacuo to give the title compound(1.50 g) as yellow oil.

Reference： [1]Current Patent Assignee: MERCK & CO INC; WUXI APPTEC CO., LTD. - WO2016/101119, 2016, A1 Location in patent: Page/Page column 92

58
[ 7295-76-3 ]
[ 93560-55-5 ]
[ 1331850-50-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 85% 2: 10%	With dichloro(N,N,N’,N‘-tetramethylethylenediamine)zinc; 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran at 20℃; for 2h;

Reference： [1]Hedidi, Madani; Erb, William; Bentabed-Ababsa, Ghenia; Chevallier, Floris; Picot, Laurent; Thiéry, Valérie; Bach, Stéphane; Ruchaud, Sandrine; Roisnel, Thierry; Dorcet, Vincent; Mongin, Florence [Tetrahedron, 2016, vol. 72, # 41, p. 6467 - 6476]

59
[ 7295-76-3 ]
(x)CH₄O*2CNS^(1-)*Cu⁽²⁺⁾ [ No CAS ]
trans-[Cu(NCS)₂(3-MeOPy)₂] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96.2%	Cooling;	General Procedure for producing crystals of trans-[Cu(NCS)2(XPy)2(MeOH)x]. General procedure: Cu(NO3)22.5H2O (0.10 g, 0.43 mmol) was dissolvedin 15 mL of MeOH at 0 C. Solid NH4SCN (0.065 g,0.86 mmol) was added to the solution, resulting in a green/brownsolution of Cu(SCN)2xMeOH. Excess XPy ligand (about 3 drops)was added, forming a green solution. The solution was cooled ina freezer until crystals formed. The supernatant was poured off and the crystals washed with ethyl ether and then air dried. In allcases the crystals in each batch were highly homogeneous inappearance. In the case of Bpy and Pyz ligands, insoluble productsare produced. In order to form crystals with these ligands a MeOHsolution of Cu(NO3)22.5H2O and NH4SCN prepared as describedabove was layered with an equal volume of MeOH solution containing0.22 mmol of ligand. Product yields and Cu analysis resultsare listed in Table 1.

Reference： [1]Handy, Joseph V.; Ayala, Gerardo; Pike, Robert D. [Inorganica Chimica Acta, 2017, vol. 456, p. 64 - 75]

60
[ 7295-76-3 ]
[ 4891-38-7 ]
methyl 4-methoxy-2-phenylpyrazolo[1,5-a]pyridine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With perchloric acid; ethyl o-mesitylsulfonylacetohydroxamic acid; potassium carbonate In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide at 20℃; for 20h;	Methyl 4-methoxy-2-phenylpyrazolo[1,5-a]pyridine-3-carboxylate (11): typical procedure To a solution of ethyl o-mesitylsulfonylacetohydroxamic acid (78.5 g, 0.275 mol) in 1,4-dioxane (69 mL) was added a 70% aqueous solution of hydrogen perchlorate (28.5 mL, 0.330 mol), and the mixture was stirred at 0°C for 0.5 h. After the addition of ice-water, the precipitate was collected. The cake was dissolved in dichloromethane (229 mL) and dried over Na2SO4. To the mixture was added a solution of 3-methoxypyridine (25.0 g, 0.229 mol) in dichloromethane (229 mL). After stirring at room temperature for 1 h, the mixture was concentrated in vacuo. To a solution of the resulting material in 10% DMF-THF (253 mL) was added potassium carbonate (63.0 g, 0.458 mol) and methyl 3-phenylpropiolate (18.0 g, 0.115 mol) at room temperature. After the addition of DMF (217 mL), the mixture was stirred at room temperature for 20 h. Water was added, and then the mixture was extracted with ethyl acetate. The combined organic layer was washed with water and brine, and then dried over sodium sulfate and concentrated in vacuo. The crude material was purified by flash column chromatography on silica gel (hexane:AcOEt = 4:1) to give methyl 4-methoxy-2-phenylpyrazolo[1,5-a]pyridine-3-carboxylate 11 as a yellow solid (11.7 g, 36%, two steps). Mp 89-91 oC. 1H NMR (400 MHz, CDCl3) δ 3.82 (3H, s), 3.97 (3H, s), 6.56 (1H, d, J = 7.3 Hz), 6.79 (1H, t, J = 7.3 Hz), 7.40-7.47 (3H, m), 7.72-7.75 (2H, m), 8.16 (1H, d, J = 7.3 Hz). IR (ATR) nmax 3114, 3009, 2949, 2838, 1716, 1637, 1554, 1523, 1466, 1411, 1329, 1256, 1135, 1096, 1049, 973, 927, 847, 810, 777, 742, 697, 663, 556, 537, 502 cm-1. MS (EI) 282 [M]+. HRMS (EI) calcd for C16H14N2O3 [M]+ 282.1004, found 282.1038.

Reference： [1]Umei, Kentaro; Nishigaya, Yosuke; Kondo, Atsushi; Tatani, Kazuya; Tanaka, Nobuyuki; Kohno, Yasushi; Seto, Shigeki [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 9, p. 2635 - 2642]

61
[ 1851-22-5 ]
[ 7295-76-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium iodide / methanol / 6 h / Reflux 2: hydrazine hydrate; pyrographite; iron(III) chloride / ethanol / 4 h / 70 °C
	Multi-step reaction with 2 steps 1: potassium iodide / methanol / 8 h / Reflux 2: hydrazine hydrate; pyrographite; iron(III) chloride / ethanol / 4 h / 70 °C

Reference： [1]Current Patent Assignee: ANHUI UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN106632006, 2017, A
[2]Current Patent Assignee: ANHUI UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN106632006, 2017, A

62
[ 7295-76-3 ]
[ 80522-42-5 ]
[ 14627-81-7 ]
C₁₉H₃₇NOSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93 %Spectr.	Stage #1: 3-methoxypyridine; triisopropylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Stage #2: di-tert-butylmagnesium In 1,4-dioxane; diethyl ether; dichloromethane at -85℃; for 16h; Inert atmosphere;	Synthesis of 4-tert-Butylpyridines; General Procedure General procedure: Trapping Reaction (GP-A)TIPSOTf (1.05 equiv) was added to a solution of the correspondingpyridine derivative (1.0 equiv) in CH2Cl2 (6 mL/mmol) and the resultingmixture was stirred at r.t. for 15 min. The solution was cooled to-85 °C, treated with 1,4-dioxane (2.2 equiv) and, after 5 min, a -85 °Ccold solution of t-Bu2Mg (2.0 equiv) was added by using a transfercannula. The reaction mixture was quenched after 16 h by the additionof water (6 mL/mmol) and saturated aqueous NaCl (10mL/mmol). The aqueous phase was extracted with CH2Cl2 (3 × 15mL/mmol), the combined organic layers were washed with saturatedaqueous NaCl (15 mL/mmol), dried over Na2SO4, and the solventswere removed under reduced pressure. Quantitative analysis of thecrude product by 1H NMR spectroscopy using 2,4,6-collidine as internalstandard revealed the amounts of the corresponding dihydropyridineand of its oxidation product. The crude material was then purifiedby flash chromatography (FC) to give the corresponding 4-tertbutyl-1,4-dihydropyridine as intermediate product.

Reference： [1]Rappenglück, Sebastian; Niessen, Karin V.; Seeger, Thomas; Worek, Franz; Thiermann, Horst; Wanner, Klaus T. [Synthesis, 2017, vol. 49, # 17, p. 4055 - 4064]

63
[ 623-73-4 ]
[ 7295-76-3 ]
[ 623-47-2 ]
diethyl 6-methoxyindolizine-1,3-dicarboxylate [ No CAS ]
diethyl 8-methoxyindolizine-1,3-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 68% 2: 4%	With meso-tetraphenylporphyrin iron(III) chloride In dichloromethane at -20 - 22℃; for 16h;

Reference： [1]Douglas, Tim; Pordea, Anca; Dowden, James [Organic Letters, 2017, vol. 19, # 23, p. 6396 - 6399]

64
[ 7295-76-3 ]
[ 106368-49-4 ]
C₁₄H₂₁NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	Stage #1: 3-methoxypyridine; 1-pentyl-1-cyclopropanol With bis(2,2’-bipyridine)silver(II) peroxydisulfate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: With ammonium peroxydisulfate In N,N-dimethyl-formamide at 0 - 20℃; for 3h; Inert atmosphere;

Reference： [1]Nikolaev, Andrei; Legault, Claude Y.; Zhang, Minhao; Orellana, Arturo [Organic Letters, 2018, vol. 20, # 3, p. 796 - 799]

65
[ 7295-76-3 ]
sodium azide [ No CAS ]
copper(II) nitrate trihydrate [ No CAS ]
catena-[Cu(3-methoxypyridine)₂(μ_1,1-N₃)₂] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	In methanol; water at 20℃;	4 2.2. Synthesis of the complexes General procedure: A general method was used to synthesize the four pyridylazido-copper(II) complexes: To a well stirred mixture containingCu(NO3)2.3H2O (0.121 g, 0.50 mmol) and the corresponding pyridylligand (4-pyridylmethanol, 4-HOCH2py; 3-methoxypyridine, 3-MeOpy; 2-bromo-4-methylpyrdine, 2-Br-4-Mepy; 2-chloro-6-methylnicotinic acid, 2-Cl-4-MeHnic, 1 mmol of each) dissolvedin methanol (20 mL), an aqueous solution of NaN3 (0.5-1.0 mmoldissolved in 5 mL H2O) was added dropwise over a period of 10min until just the appearance of a brown color or a precipitate ofCu(N3)2. The mixture was allowed to stand at room temperaturefor 2-3 h, then the brown precipitate was filtered off through Celiteand the resulting green solution was allowed to crystallize at roomtemperature. After 1-3 days, the green crystalline compoundwhich separated was collected by filtration, washed with propan-2-ol, Et2O and dried in air. Single crystals were obtained fromdilute solutions. The complexes were characterized as follows:

Reference： [1]Louka, Febee R.; Massoud, Salah S.; Haq, Tamim K.; Koikawa, Masayuki; Mikuriya, Masahiro; Omote, Masataka; Fischer, Roland C.; Mautner, Franz A. [Polyhedron, 2017, vol. 138, p. 177 - 184]

66
[ 7295-76-3 ]
[ 52605-96-6 ]

Yield	Reaction Conditions	Operation in experiment
10.20 g	With hydrogenchloride; potassium permanganate; In water; at 0 - 15℃;	(1) Dissolving 10.91 g (0.1 mol) of 3-methoxypyridine in 121.53 g (containing 1.0 mol of hydrogen chloride) of 30.0% hydrochloric acid,Under stirring, the temperature was controlled at 0-15 C., and 11.83 g of a 25.0% potassium manganate solution was added dropwise. After the dropwise addition was completed, the reaction temperature was controlled at 0-15 C. to carry out the chlorination reaction of the reaction system.During the reaction, samples were taken at regular intervals and detected with high performance liquid chromatography.When it was detected that the mass of 2-chloro-3-methoxypyridine in the reaction system accounted for 80.5% of the total mass of organic substances in the reaction system,The reaction was terminated by adding 11.36 g (0.06 mol) of stannous chloride to obtain a feed solution containing 2-chloro-3-methoxypyridine; (2) 71.8 g of methylene chloride was added to the reaction mixture, and the mixture was stirred and extracted for 2 hours. The mixture was allowed to stand for 1 hour and the organic phase was taken and allowed to cool down to -15C to -5C.The solids were extracted and analyzed from the organic phase. The resulting 10.20 g of solid was 2-chloro-3-methoxypyridine. The yield was calculated to be 71%. After the determination, the main content was 98.0%.

Reference： [1]Patent: CN107954913,2018,A .Location in patent: Paragraph 0018

67
[ 7295-76-3 ]
trans-[OsCl₂(η²-C₂H₄){(S,S)-ⁱPr-(2,6-bis[4′-(S)-isopropyloxazolin-2′-yl]pyridine)}] [ No CAS ]
trans-[OsCl₂(3-MeO-py){2,6-bis[4’-(S)-isopropyloxazolin-2-yl]pyridine}] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	In toluene for 1.5h; Reflux; Inert atmosphere; Schlenk technique;	4.4. Synthesis of complexes trans-[OsCl2(L){(S,S)-iPr-pybox}] General procedure: To a solution of complex trans-[OsCl2(η2-C2H4){(S,S)-iPr-pybox}](2) (0.100 g, 0.17 mmol) in toluene (25 mL) the corresponding ligand(0.26 mmol) was added and the mixture heated under reflux during90 min. The solvent was then evaporated under reduced pressure andhexane (20 mL) was added yielding a solid that was washed withhexane (3×5 mL) and vacuum-dried.

Reference： [1]de Julián, Eire; Fernández, Nuria; Díez, Josefina; Lastra, Elena; Gamasa, M. Pilar [Molecular catalysis, 2018, vol. 456, p. 75 - 86]

68
[ 7295-76-3 ]
[ 143300-64-5 ]
N,N-diethyl-1-(pyridin-3-yl)piperidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium hydride; lithium iodide In tetrahydrofuran at 0 - 60℃; for 7h; Inert atmosphere; Sealed tube;

Reference： [1]Pang, Jia Hao; Kaga, Atsushi; Chiba, Shunsuke [Chemical Communications, 2018, vol. 54, # 73, p. 10324 - 10327]

69
[ 7295-76-3 ]
[ 4897-50-1 ]
1'-(pyridin-3-yl)-1,4'-bipiperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium hydride; lithium iodide In tetrahydrofuran at 0 - 60℃; for 24h; Inert atmosphere; Sealed tube;

Reference： [1]Pang, Jia Hao; Kaga, Atsushi; Chiba, Shunsuke [Chemical Communications, 2018, vol. 54, # 73, p. 10324 - 10327]

70
[ 123-75-1 ]
[ 7295-76-3 ]
[ 69698-09-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium hydride; lithium iodide In tetrahydrofuran at 0 - 60℃; for 4h; Inert atmosphere; Sealed tube;

Reference： [1]Pang, Jia Hao; Kaga, Atsushi; Chiba, Shunsuke [Chemical Communications, 2018, vol. 54, # 73, p. 10324 - 10327]

71
[ 7295-76-3 ]
[ 75-36-5 ]
C₈H₁₀NO₂⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-methoxypyridine With copper(l) iodide; dimethylsulfide In tetrahydrofuran at -20 - 20℃; for 0.25h; Stage #2: acetyl chloride In tetrahydrofuran for 0.25h;	3.3. General Procedure for the Synthesis of Compounds 2 General procedure: First, 10 mmol of the respective pyridine were dissolved in 50 mL of dried THF. After additionof 0.5 mmol of copper(I) iodide and 3 mL of dimethyl sulphide, the mixture was stirred at room temperature until a clear solution resulted. Then, it was cooled down to -20 °C. After 15 min, 10 mmolof acetyl chloride were added dropwise and stirring continued for 15 min. Then, 10 mmol of phenylmagnesium chloride were added and stirring followed for additional 15 min. Then, the mixturewarmed up to room temperature. Then, 50 mL of an ammonium chloride solution (20%) were addedand extraction with diethyl ether followed with portions of 50, 25 and again 25 mL. The unified organiclayer was extracted with each 50 mL of a solution of ammonium chloride in ammonia for two times,with 50 mL water, hydrochloric acid (10%) for two times, water and finally a saturated solution ofsodium chloride in water. The organic layer was then dried over sodium sulphate, filtered and finallyremoved under reduced pressure to give an oily substance that partially crystallized from methanol.

Reference： [1]Holzer, Max; Schade, Nico; Opitz, Ansgar; Hilbrich, Isabel; Stieler, Jens; Vogel, Tim; Neukel, Valentina; Oberstadt, Moritz; Totzke, Frank; Schchtele, Christoph; Sippl, Wolfgang; Hilgeroth, Andreas [Molecules, 2018, vol. 23, # 9]

72
[ 7295-76-3 ]
[ 13505-07-2 ]

Yield	Reaction Conditions	Operation in experiment
86 g	With nitric acid; acetic acid at 20℃; for 6h; Cooling with ice;	1.2; 2.2; 3.2 Step 2, preparation of 4-nitro-3-methoxypyridine: In an ice bath, 72 g of 3-methoxypyridine was dissolved in 150 mL of glacial acetic acid.120g concentrated nitric acid was added dropwise to carry out the nitration reaction. After the addition was completed,The reaction system is heated to room temperature for 6 h, after the reaction is completed,The reaction system was slowly poured into ice water, and glacial acetic acid was recovered by a conventional operation.Drying a yellow solid 86g.

Reference： [1]Current Patent Assignee: JIANGSU COLLEGE OF ENGINEERING AND TECHNOLOGY - CN108892635, 2018, A Location in patent: Paragraph 0026; 0028; 0032; 0034; 0038; 0040; 0044; 0045

73
[ 7295-76-3 ]
[ 61676-62-8 ]
[ 1243312-43-7 ]

Yield	Reaction Conditions	Operation in experiment
		Starting material 3-methoxypyridine VIII (5.0 g, 45.8 mol, 1.0 equiv.)Soluble in 100 ml of Et2O,Add 1.3 equiv. LDA in THF at -100 C.After adding the insulation reaction for 1 hour,Add isopropanol pinacol borate (11.08g, 59.5 mmol, 1.3 equiv.) after 2 hours of incubation,After quenching with water, the reaction was returned to room temperature and stirred for 1 h.Adjust the pH to between 3 and 4, spin dry the aqueous phase, and use the crude product directly for the next reaction.

Reference： [1]Patent: CN110015987,2019,A .Location in patent: Paragraph 0027

74
[ 7295-76-3 ]
[ 1461-22-9 ]
3-methoxy-4-(tributyltin)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-methoxypyridine With lithium diisopropyl amide In tetrahydrofuran at -70℃; for 1h; Stage #2: tributyltin chloride In tetrahydrofuran for 2h;	3 Example 3 Synthesis of the compound 3-methoxy-4-(tributyltin)pyridine XII-3: The starting material 3-methoxypyridine VIII (5.0 g, 45.8 mol, 1.0 equiv.) was dissolved in 100 ml of THF.Add 1.1 equiv. LDA in THF at -70 °C.After adding the insulation reaction for 1 hour,Adding tributyltin chloride (13.42 g, 41.2 mmol, 0.9 equiv.) and adding the incubation reaction for 2 h,The reaction was quenched with water, returned to room temperature, and concentrated to remove solvent.The crude product was used directly in the next reaction.

Reference： [1]Current Patent Assignee: NANJING SYNTITAN PHARMACEUTICAL - CN110015987, 2019, A Location in patent: Paragraph 0029

75
[ 7295-76-3 ]
[ 5419-55-6 ]
[ 1008506-24-8 ]

Yield	Reaction Conditions	Operation in experiment
		The starting material 3-methoxypyridine VIII (6.50 g, 59.6 mmol, 1.0 equiv.)Soluble in 50 ml of THF,Add 1.3 equiv. LDA in THF at -70 C.After the addition of the incubation reaction for 1 h, B(Oi-Pr)3 (14.56 g, 77.4 mmol, 1.3 equiv.) was added dropwise.After the addition of the incubation reaction for 2 h, the reaction was quenched with water.After stirring to room temperature for 1 h, adjust the pH to between 3 and 4, and spin dry the aqueous phase.The crude product was used directly in the next reaction.

Reference： [1]Patent: CN110015987,2019,A .Location in patent: Paragraph 0025

76
[ 7295-76-3 ]
C₁₄H₂₀B₉^(1-)*C₄H₁₂N⁽¹⁺⁾ [ No CAS ]
C₂₀H₂₆B₉NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dimethoxyethane at 20℃; Inert atmosphere; Schlenk technique;
75%	With tetramethlyammonium chloride In 1,2-dimethoxyethane; water at 20℃; for 3h; Electrochemical reaction; regioselective reaction;

Reference： [1]Yang, Zhongming; Zhao, Weijia; Liu, Wei; Wei, Xing; Chen, Meng; Zhang, Xiao; Zhang, Xiaolei; Liang, Yong; Lu, Changsheng; Yan, Hong [Angewandte Chemie - International Edition, 2019, vol. 58, # 34, p. 11886 - 11892][Angew. Chem., 2019, vol. 131, # 34, p. 12012 - 12018,7]
[2]Yang, Long; Bongsuiru Jei, Becky; Scheremetjew, Alexej; Kuniyil, Rositha; Ackermann, Lutz [Angewandte Chemie - International Edition, 2021, vol. 60, # 3, p. 1482 - 1487][Angew. Chem., 2021, vol. 133, # 3, p. 1504 - 1509,6]

77
[ 7295-76-3 ]
[ 66003-33-6 ]
C₁₄H₂₃N₂O₂⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75.1%	In acetonitrile Reflux;	20 Example 20 Compound 1 (0.82 g, 4.58 mmol) was dissolved in 10 mL of acetonitrile.Add 3-methoxypyridine (0.50 g, 0.46 mL, 4.58 mmol) and heat to reflux overnight.After removing the solvent under vacuum, silica gel column separation was performed.The product-containing liquid was collected using methanol / dichloromethane (15/85, v / v) as the eluent.The solvent was removed under vacuum to give compound 14 as a white solid (0.99 g, 75.1%).

Reference： [1]Current Patent Assignee: DALIAN UNIVERSITY OF TECHNOLOGY - CN110372533, 2019, A Location in patent: Paragraph 0094-0096

78
[ 7295-76-3 ]
[ 1942-46-7 ]
(E)-4-(dec-5-en-5-yl)-3-methoxypyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With cobalt(III) acetylacetonate; 1,3-bis-(diphenylphosphino)propane; bis(2,6-di-tert-butyl-4-methylphenoxide)methylaluminum In n-heptane; toluene at 100℃; for 24h; Inert atmosphere;

Reference： [1]Di Monaco, Sabrina; Pang, Benjamin Piaoxiang; Rahman, Md. Shafiqur; Thai, Anh Ngoc; Wang, Chang-Sheng; Wang, Chen; Yoshikai, Naohiko [Journal of the American Chemical Society, 2020, vol. 142, # 29, p. 12878 - 12889]

79
[ 7295-76-3 ]
[ 143-15-7 ]
1-dodecyl-3-methoxypyridinium bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In acetonitrile for 48h; Reflux;	6.1.2. General procedure for synthesis of monoquaternary salts 1-15 General procedure: 1-Bromoalkane (28.93 mmol)was added to nitrogen-containingheterocycles compound (20.67 mmol) in acetonitrile (30 mL) underroom temperature conditions. The reaction mixture was then stirredunder reflux for 48 h. The solvent was evaporated underreduced pressure, and the crude product purified by crystallizationfrom diethyl ether, filtered, washed with diethyl ether and allowedto dry at room temperature. The salts 6 and 8 were purified bycrystallization from acetone. See the Supplementary Informationfor more details and NMR spectra for each of the novel compound.6.1.2.1. 4-Carbamoyl-1-dodecylpyridinium bromide (1a).Compound 1a was isolated as white solid; Yield 89%

Reference： [1]Benkova, Marketa; Bostik, Pavel; Bostikova, Vanda; Dolezal, Rafael; Gunde-Cimerman, Nina; Hobzova, Lenka; Hympanova, Michaela; Jun, Daniel; Korabecny, Jan; Malinak, David; Marek, Jan; Markova, Aneta; Prchal, Lukas; Ryskova, Lenka; Salajkova, Sarka; Sleha, Radek; Soukup, Ondrej; Sepčić, Kristina [European Journal of Medicinal Chemistry, 2020, vol. 206]

80
[ 7295-76-3 ]
[ 112-71-0 ]
3-methoxy-1-tetradecylpyridinium bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In acetonitrile for 48h; Reflux;	6.1.2. General procedure for synthesis of monoquaternary salts 1-15 General procedure: 1-Bromoalkane (28.93 mmol)was added to nitrogen-containingheterocycles compound (20.67 mmol) in acetonitrile (30 mL) underroom temperature conditions. The reaction mixture was then stirredunder reflux for 48 h. The solvent was evaporated underreduced pressure, and the crude product purified by crystallizationfrom diethyl ether, filtered, washed with diethyl ether and allowedto dry at room temperature. The salts 6 and 8 were purified bycrystallization from acetone. See the Supplementary Informationfor more details and NMR spectra for each of the novel compound.6.1.2.1. 4-Carbamoyl-1-dodecylpyridinium bromide (1a).Compound 1a was isolated as white solid; Yield 89%

81
[ 7295-76-3 ]
[ 112-82-3 ]
1-hexadecyl-3-methoxypyridinium bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In acetonitrile for 48h; Reflux;	6.1.2. General procedure for synthesis of monoquaternary salts 1-15 General procedure: 1-Bromoalkane (28.93 mmol)was added to nitrogen-containingheterocycles compound (20.67 mmol) in acetonitrile (30 mL) underroom temperature conditions. The reaction mixture was then stirredunder reflux for 48 h. The solvent was evaporated underreduced pressure, and the crude product purified by crystallizationfrom diethyl ether, filtered, washed with diethyl ether and allowedto dry at room temperature. The salts 6 and 8 were purified bycrystallization from acetone. See the Supplementary Informationfor more details and NMR spectra for each of the novel compound.6.1.2.1. 4-Carbamoyl-1-dodecylpyridinium bromide (1a).Compound 1a was isolated as white solid; Yield 89%

82
[ 7295-76-3 ]
[ 73183-34-3 ]
[ 445264-60-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: bis(pinacol)diborane With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C₅₁H₃₂N₈Zn In para-xylene at 20℃; for 0.5h; Schlenk technique; Stage #2: 3-methoxypyridine In para-xylene at 80℃; for 24h; Schlenk technique; regioselective reaction;

Reference： [1]Al-Shehimy, Shaymaa; Gramage-Doria, Rafael; Roisnel, Thierry; Trouvé, Jonathan; Zardi, Paolo [Angewandte Chemie - International Edition, 2021, vol. 60, # 33, p. 18006 - 18013][Angew. Chem., 2021, vol. 133, # 33, p. 18154 - 18161]

83
[ 7295-76-3 ]
[ 1942-45-6 ]
C₁₄H₂₁NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; triisobutylaluminum; 3-(2-hydroxyethyl)-1-(4-methoxy-2,6-dimethylphenyl)-4,5-dimethyl-1H-imidazol-3-ium bromide; sodium t-butanolate In toluene at 100℃; for 12h; Inert atmosphere;	A typical procedure for Ni-catalysed C3-alkenylation: General procedure: to a 15 ml oven-dried tube were added ligand L10 (14.5 mg, 10 mol%), Ni(cod) 2 (11.0 mg, 10 mol%) and t BuONa (4.6 mg, 12.5 mol%) and dry degassed toluene (1.0 ml) under a N 2 atmosphere. The mixture solution was stirred at 80 °C in a dry block heater for 30 min and then cooled down to room temperature. The pyridine derivative (0.4 mmol, 1 equiv.), Al i Bu 3 (1.1 M in 36.3 μl of toluene, 10 mol%) and alkyne (1.2 mmol, 3 equiv.) were added, and the tube was sealed and stirred at 100 °C in a dry block heater for 12 h. After that, the mixture was cooled to room temperature, quenched with 2 ml of 5% ethylenediamine tetraacetic acid disodium salt solution, filtered through a short plug of silica gel (EtOAc as the eluent) and concentrated in vacuo to afford a crude product. Further purification by flash column chromatography on silica gel (eluting with EtOAc/hexanes) gave the pure product.

Reference： [1]Zhang, Tao; Luan, Yu-Xin; Lam, Nelson Y. S.; Li, Jiang-Fei; Li, Yue; Ye, Mengchun; Yu, Jin-Quan [Nature Chemistry, 2021, vol. 13, # 12, p. 1207 - 1213]

84
[ 7295-76-3 ]
[ 1942-45-6 ]
(E)-3-methoxy-5-(oct-4-en-4-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; triisobutylaluminum; 3-(2-hydroxyethyl)-1-(4-methoxy-2,6-dimethylphenyl)-4,5-dimethyl-1H-imidazol-3-ium bromide; sodium t-butanolate In toluene at 100℃; for 12h; Inert atmosphere;	10 Example 10: Synthesis of (E)-3-Methoxy-5-(oct-4-en-4-yl)pyridin Add Ni(cod)2(11.0mg, 0.04mmol), NHC·HBr (14.5mg, 0.04mmol), sodium tert-butoxide (4.6mg, 0.05mmol) in dry and degassed toluene (2.0mL) in the reaction flask.), stirred at 80°C for 30mins and then cooled to room temperature. Add substrate 3c (0.4mmol), triisobutylaluminum (0.04mmol, 36.3μL, 1.1M in toluene), and substrate 4a (1.2mmol), nitrogen The reaction was carried out at 100°C for 12 hours.After the reaction was completed, celite was filtered, silica gel column chromatography, and the eluent was (ethyl acetate/petroleum ether = 1/20 to 1/10) to obtain 54.3 mg of yellow oily liquid 5c with a yield of 62%.

Reference： [1]Current Patent Assignee: NANKAI UNIVERSITY - CN113527212, 2021, A Location in patent: Paragraph 0060-0062

85
[ 7295-76-3 ]
[ 1131-48-2 ]
[ 407-25-0 ]
3-methoxy-5'-phenyl-[1,2'-bipyridin]-1-ium 2,2,2-trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	In dichloromethane at 0 - 20℃; regioselective reaction;	General Procedure A: Synthesis of Pyridinium Salts from Pyridine N-Oxides; General procedure: To a stirred solution of pyridine N-oxide and pyridine (5.0-10.0 equiv.) in CH2Cl2 or CH3CN(0.1-0.2 M) was added trifluoroacetic anhydride (2.0-3.0 equiv.) at 0 °C. The resulting mixturewas stirred at room temperature, and reaction progress was monitored by LCMS. Uponcompletion, the reaction mixture was concentrated, dissolved in a minimal amount of CH2Cl2,and triturated from rapidly stirring Et2O. The crude pyridinium salt was isolated by filtration and washed with Et2O. The pyridinium salt, or the crude mixture (when solid pyridinium saltswere not formed) was purified by chromatography on silica gel (MeOH/CH2Cl2) or reversedphaseC18 (CH3CN/H2O) to afford the title compound.

Reference： [1]Xiong, Hui; Hoye, Adam T. [Synlett, 2022, vol. 33, # 4, p. 371 - 375]

86
[ 7295-76-3 ]
[ 623-47-2 ]
[ 909717-95-9 ]

Yield	Reaction Conditions	Operation in experiment
52.29%	Stage #1: 3-methoxypyridine With 2,4-dinitrophenylhydroxylamine In acetonitrile at 40℃; for 4h; Stage #2: propynoic acid ethyl ester With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 16h;	338.a Step a: To a solution of 3-methoxypyridine (500 mg, 4.58 mmol) in MeCN (10 mL) was added 2,4-dinitrophenyl) hydroxylamine (760.26 mg, 3.82 mmol) and the reaction stirred at 40° C. for 4 h. The mixture was filtered and concentrated in vacuo to give an orange solid, 1.18 g. This was dissolved in DMF (3 mL), K2CO3 (529.34 mg, 3.83 mmol) and ethyl propiolate (450.87 mg, 4.60 mmol) and the reaction stirred at 25° C. for 16 h. The reaction mixture was diluted with water (30 mL) and extracted with EtOAc (100 mL×3). The combined organic extracts were washed with brine (100 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (PE/EtOAc=10/1 to 1/1) to give ethyl 4-methoxypyrazolo[1,5-a]pyridine-3-carboxylate (490 mg, 52.29% yield) as a brown oil. 1H NMR (500 MHz, CDCl3) δ ppm 1.37 (t, J=7.0 Hz, 3H), 3.98 (s, 3H), 4.33 (q, J=7.0 Hz, 2H), 6.63 (d, J=7.5 Hz, 1H), 6.83-6.79 (m, 1H), 8.15 (d, J=6.5 Hz, 1H), 8.34 (s, 1H).
	With hydroxylamine	338.a Example 338 Step a: To a solution of 3-methoxypyridine (500 mg, 4.58 mmol) in MeCN (10 mL) was added 2,4-dinitrophenyl)hydroxylamine (760.26 mg, 3.82 mmol) and the reaction stirred at 40° C. for 4 h. The mixture was filtered and concentrated in vacuo to give an orange solid, 1.18 g. This was dissolved in DMF (3 mL), K2CO3 (529.34 mg, 3.83 mmol) and ethyl propiolate (450.87 mg, 4.60 mmol) and the reaction stirred at 25° C. for 16 h. The reaction mixture was diluted with water (30 mL) and extracted with EtOAc (100 mL*3). The combined organic extracts were washed with brine (100 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (PE/EtOAc=10/1 to 1/1) to give ethyl 4-methoxypyrazolo[1,5-a]pyridine-3-carboxylate (490 mg, 52.29% yield) as a brown oil. 1H NMR (500 MHz, CDCl3) δ ppm 1.37 (t, J=7.0 Hz, 3H), 3.98 (s, 3H), 4.33 (q, J=7.0 Hz, 2H), 6.63 (d, J=7.5 Hz, 1H), 6.83-6.79 (m, 1H), 8.15 (d, J=6.5 Hz, 1H), 8.34 (s, 1H).

Reference： [1]Current Patent Assignee: BIOGEN IDEC INC. - US2022/89592, 2022, A1 Location in patent: Paragraph 1145; 1146
[2]Current Patent Assignee: BIOGEN IDEC INC. - US2022/89592, 2022, A1

87
[ 7295-76-3 ]
[ 25015-63-8 ]
5-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With C₂₈H₄₉OSiY In toluene at 60℃; for 24h; Glovebox; Inert atmosphere;

Reference： [1]Jiang, Shengjie; Luo, Yuncong; Xu, Xin [Angewandte Chemie - International Edition, 2022, vol. 61, # 21][Angew. Chem., 2022, vol. 134, # 21]

88
[ 100-42-5 ]
[ 7295-76-3 ]
C₁₄H₁₅INO⁽¹⁺⁾*I₃^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With iodine at 25℃; for 0.0833333h;

Reference： [1]Fan, Weibin; Huang, Deguang; Li, Yinghua; Zhang, Wei; Zhang, Yuan [ChemSusChem, 2022]

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[ CAS No. 7295-76-3 ] {[proInfo.proName]}

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[ 7295-76-3 ] Synthesis Path-Upstream 1~9

[ 7295-76-3 ] Synthesis Path-Downstream 1~88

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Ethers

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Pyridines

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