[ CAS No. 2743-90-0 ]

Name: 2743-90-0|1,2,3,6-Tetrahydro-2,3'-bipyridine|95%
Brand: Ambeed
SKU: A782329
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Product Details of [ 2743-90-0 ]

CAS No. :	2743-90-0	MDL No. :	MFCD00078278
Formula :	C₁₀H₁₂N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	160.22 g/mol	Pubchem ID :	-
Synonyms :

Safety of [ 2743-90-0 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P301+P330+P331+P310	UN#:	2810
Hazard Statements:	H301	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 2743-90-0 ]

Downstream synthetic route of [ 2743-90-0 ]

[ 2743-90-0 ] Synthesis Path-Downstream 1~24

1
[ 122-04-3 ]
[ 2743-90-0 ]
(<i>R</i>)-1-(4-Nitro-benzoyl)-1,2,3,6-tetrahydro-[2,3']bipyridyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 6,6′-dinitro[1,1′-biphenyl]-2,2′-dicarboxylic acid

Reference： [1]Spaeth; Kesztler [Chemische Berichte, 1937, vol. 70, p. 704,707]

2
[ 122-04-3 ]
[ 2743-90-0 ]
(<i>S</i>)-1-(4-Nitro-benzoyl)-1,2,3,6-tetrahydro-[2,3']bipyridyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 6,6′-dinitro[1,1′-biphenyl]-2,2′-dicarboxylic acid

Reference： [1]Spaeth; Kesztler [Chemische Berichte, 1937, vol. 70, p. 704,707]

3
[ 122-04-3 ]
[ 2743-90-0 ]
(+/-)-1-(4-Nitro-benzoyl)-1,2,3,6-tetrahydro-[2,3']bipyridyl [ No CAS ]

Reference： [1]Spaeth; Kesztler [Chemische Berichte, 1937, vol. 70, p. 704,707]

4
[ 2743-90-0 ]
[ 581-50-0 ]

Reference： [1]Archives of Biochemistry,1959,vol. 80,p. 258,263

5
[ 2743-90-0 ]
[ 581-49-7 ]

Yield	Reaction Conditions	Operation in experiment
	With 6,6′-dinitro[1,1′-biphenyl]-2,2′-dicarboxylic acid

Reference： [1]Spaeth; Kesztler [Chemische Berichte, 1937, vol. 70, p. 704,707]

6
[ 1027559-83-6 ]
[ 2743-90-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; potassium hydroxide; potassium carbonate 1.) THF, hexane, water, 15-20 min, room temp., 2.) water, pH 10-12; Yield given. Multistep reaction;
	Stage #1: Benzhydrylidene-((Z)-5-chloro-1-pyridin-3-yl-pent-3-enyl)-amine With hydrogenchloride; water Stage #2: With potassium carbonate; potassium hydroxide In water	3.F.iii; 3.F.iv Steps 2i to 2iii alternate route: Conversion of Formula Ito Anatabine using LDAFormula I was prepared according to Example 1. LDA was added to Formula I at -10 to 0° C. Cis-1,4-dichloro-2-butene was added at -78° C. to -45° C. Steps 2ii and 2iii were performed according to Example 2.

Reference： [1]Deo, Niranjan M.; Crooks, Peter A. [Tetrahedron Letters, 1996, vol. 37, # 8, p. 1137 - 1140]
[2]Current Patent Assignee: PHILIP MORRIS INTERNATIONAL INC. - US2011/237627, 2011, A1 Location in patent: Page/Page column 5

7
[ 2743-90-0 ]
[ 13078-04-1 ]

Yield	Reaction Conditions	Operation in experiment
83%	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; under 760.051 Torr; for 3h;	A solution of 1,2,3,6-tetrahydro-2,3'-bipyridine (6) (29.3 mg, 0.18 mmol) in anhydrous MeOH (1.8 mL) containing Pd/C (10% Pd) (9.7 mg, 5 mol%) was hydrogenated (pH2 = 1 atm) at room temperature for 3 h. The mixture was filtered through a pad of Celite and the filtrate concentrated to yield anabasine (24.3 mg, 0.15 mmol, 83%) as a light yellow oil. 1H NMR (600.13 MHz, CDCl3, 25 C): delta = 8.59 (dd, Jo',m = 0.8 Hz, Jo',p = 2.3 Hz, 1 H, Ho'), 8.49 (dd, Jo,p = 1.7 Hz, Jo,m = 4.8 Hz, 1 H, Ho), 7.72 (ddd, Jp,o = 1.7 Hz, Jp,o' = 2.3 Hz, Jp,m = 7.9 Hz, 1 H, Hp), 7.25 (ddd, Jm,o' = 0.8 Hz, Jm,o = 4.8 Hz, Jm,p = 7.9 Hz, 1 H, Hm), 3.64 (dd, JCH,CH2a-4 = 2.7 Hz, JCH,CH2b-4 = 11.1 Hz, 1 H, CH), 3.21 (dddd, JCH2a-1,CH2a-3 = -1.5 Hz, JCH2a-1,CH2a-2 = 2.6 Hz, JCH2a-1,CH2b-2 = 4.1 Hz, JCH2a-1,CH2b-1 = -11.6 Hz, 1 H, CH2a-1), 2.81 (ddd, JCH2b-1,CH2a-2 = 2.7 Hz, JCH2b-1,CH2a-1 = -11.6 Hz, JCH2b-1,CH2b-2 = 12.2 Hz, 1 H, CH2b-1), 1.91 (dddddd, JCH2a-3,CH2a-1 = -1.5 Hz, JCH2a-3,CH2a-2 = 2.6 Hz, JCH2a-3,CH2a-4 = 3.0 Hz, JCH2a-3,CH2b-4 = 3.7 Hz, JCH2a-3,CH2b-2 = 4.1 Hz, JCH2a-3,CH2b-3 = -13.5 Hz, 1 H, CH2a-3), 1.79 (ddddd, JCH2a-4,CH2a-2 = -1.6 Hz, JCH2a-4,CH = 2.7 Hz, JCH2a-4,CH2a-3 = 3.0 Hz, JCH2a-4,CH2b-3 = 4.0 Hz, JCH2a-4,CH2b-4 = -13.2 Hz, 1 H, CH2a-4), 1.68 (dddddd, JCH2a-2,CH2a-4 = -1.6 Hz, JCH2a-2,CH2a-1 = 2.6 Hz, JCH2a-2,CH2a-3 = 2.6 Hz, JCH2a-2,CH2b-1 = 2.7 Hz, JCH2a-2,CH2b-3 = 3.9 Hz, JCH2a-2,CH2b-2 = -13.2 Hz, 1 H, CH2a-2), 1.55 (ddddd, JCH2b-2,CH2a-1 = 4.1 Hz, JCH2b-2,CH2a-3 = 4.1 Hz, JCH2b-2,CH2b-1 = 12.2 Hz, JCH2b-2,CH2b-3 = 12.8 Hz, JCH2b-2,CH2a-2 = -13.2 Hz, 1 H, CH2b-2), 1.52 (dddd, JCH2b-4, CH2a-3 = 3.7 Hz JCH2b-4,CH = 11.1 Hz, JCH2b-4,CH2b-3 = 12.9 Hz, JCH2b-4,CH2a-4 = -13.2 Hz, 1 H, CH2b-4), 1.51 (ddddd, JCH2b-3,CH2a-2 = 3.9 Hz, JCH2b-3,CH2a-4 = 4.0 Hz, JCH2b-3,CH2b-2 = 12.8 Hz, JCH2b-3,CH2b-4 = 12.9 Hz, JCH2b-3,CH2a-3 = -13.5 Hz, 1 H, CH2b-3) ppm. 13C NMR (150.9 MHz, CDCl3, 25 C): delta = 148.7 (Co'), 148.6 (Co), 140.6 (Cm'), 134.2 (Cp), 123.5 (Cm), 59.8 (CH), 47.6 (CH2-1), 34.8 (CH2-4), 25.7 (CH2-2), 25.2 (CH2-3) ppm. HRMS calcd. for C10H15N2 [M+H]+: 163.1235, found: 163.1238.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 4619 - 4621
[2]Canadian Journal of Chemistry,1997,vol. 75,p. 616 - 620

Yield	Reaction Conditions	Operation in experiment
	Rk. m. Pd/C (200grad, 20 Min.) -> 2,3'-Bipyridin;

Yield	Reaction Conditions	Operation in experiment
59%	With pyridine; water for 72h; Ambient temperature;

11
[ 3731-52-0 ]
[ 2743-90-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: benzene / 16 h / Heating 2: 2.4 M n-BuLi, diisopropylamine / tetrahydrofuran; hexane / -78 - -45 °C 3: 1.) 10percent aq. HCl, 2.) K₂CO₃, 40percent aq. KOH / 1.) THF, hexane, water, 15-20 min, room temp., 2.) water, pH 10-12
	Multi-step reaction with 2 steps 1.1: toluene-4-sulfonic acid / toluene / 12 h / 110 °C 2.1: lithium dipropan-2-ylazanide / tetrahydrofuran / 0.5 h / -78 - -60 °C 2.2: 1 h / -60 °C

Reference： [1]Deo, Niranjan M.; Crooks, Peter A. [Tetrahedron Letters, 1996, vol. 37, # 8, p. 1137 - 1140]
[2]Current Patent Assignee: PHILIP MORRIS INTERNATIONAL INC. - WO2021/260029, 2021, A1

12
[ 175441-83-5 ]
[ 2743-90-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 2.4 M n-BuLi, diisopropylamine / tetrahydrofuran; hexane / -78 - -45 °C 2: 1.) 10percent aq. HCl, 2.) K₂CO₃, 40percent aq. KOH / 1.) THF, hexane, water, 15-20 min, room temp., 2.) water, pH 10-12

Reference： [1]Deo, Niranjan M.; Crooks, Peter A. [Tetrahedron Letters, 1996, vol. 37, # 8, p. 1137 - 1140]

13
[ 1236361-13-9 ]
[ 2743-90-0 ]

Yield	Reaction Conditions	Operation in experiment
44%	With ferrous(II) sulfate heptahydrate In methanol at 10℃; for 3h;

Reference： [1]Location in patent: experimental part Rouchaud, Anne; Kem, William R. [Journal of Heterocyclic Chemistry, 2010, vol. 47, # 3, p. 569 - 581]

14
[ 500-22-1 ]
[ 2743-90-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: toluene / 45 h / Reflux; Inert atmosphere 2.1: zinc / tetrahydrofuran / 20 °C / Inert atmosphere 3.1: Trimethylenediamine / 1 h / Reflux; Inert atmosphere 4.1: potassium hydroxide / N,N-dimethyl-formamide / 0.25 h / Inert atmosphere 4.2: 0.25 h / 20 °C / Inert atmosphere 5.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; toluene-4-sulfonic acid / dichloromethane / 18 h / 20 °C / Inert atmosphere
	Multi-step reaction with 5 steps 1.1: 2-methyltetrahydrofuran / 3 h / 20 °C / Molecular sieve 2.1: indium / ethanol / 4 h / 0 - 20 °C 3.1: potassium carbonate / 2-methyltetrahydrofuran / 24 h / 50 °C 4.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C 4.2: 3 h / 20 °C 5.1: trifluoroacetic acid / dichloromethane / 8 h / 0 °C
	Multi-step reaction with 6 steps 1.1: 2-methyltetrahydrofuran / 3 h / 20 °C / Molecular sieve 2.1: indium / ethanol / 4 h / 0 - 20 °C 3.1: potassium carbonate / 2-methyltetrahydrofuran / 24 h / 50 °C 4.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C 4.2: 3 h / 20 °C 5.1: dichloromethane / 3 h / 20 °C 6.1: sodium hydroxide / tetrahydrofuran; water / 2 h / 20 °C

Reference： [1]Saloranta, Tiina; Leino, Reko [Tetrahedron Letters, 2011, vol. 52, # 36, p. 4619 - 4621]
[2]Rossi, Federico V.; Ballini, Roberto; Barboni, Luciano; Allegrini, Pietro; Palmieri, Alessandro [Synthesis, 2018, vol. 50, # 9, p. 1921 - 1925]
[3]Rossi, Federico V.; Ballini, Roberto; Barboni, Luciano; Allegrini, Pietro; Palmieri, Alessandro [Synthesis, 2018, vol. 50, # 9, p. 1921 - 1925]

15
[ 1332337-77-5 ]
[ 2743-90-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: zinc / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: Trimethylenediamine / 1 h / Reflux; Inert atmosphere 3.1: potassium hydroxide / N,N-dimethyl-formamide / 0.25 h / Inert atmosphere 3.2: 0.25 h / 20 °C / Inert atmosphere 4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; toluene-4-sulfonic acid / dichloromethane / 18 h / 20 °C / Inert atmosphere

Reference： [1]Saloranta, Tiina; Leino, Reko [Tetrahedron Letters, 2011, vol. 52, # 36, p. 4619 - 4621]

16
[ 1332337-78-6 ]
[ 2743-90-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: Trimethylenediamine / 1 h / Reflux; Inert atmosphere 2.1: potassium hydroxide / N,N-dimethyl-formamide / 0.25 h / Inert atmosphere 2.2: 0.25 h / 20 °C / Inert atmosphere 3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; toluene-4-sulfonic acid / dichloromethane / 18 h / 20 °C / Inert atmosphere

Reference： [1]Saloranta, Tiina; Leino, Reko [Tetrahedron Letters, 2011, vol. 52, # 36, p. 4619 - 4621]

17
[ 1332337-79-7 ]
[ 2743-90-0 ]

Yield	Reaction Conditions	Operation in experiment
60%	With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; toluene-4-sulfonic acid In dichloromethane at 20℃; for 18h; Inert atmosphere;	1,2,3,6-Tetrahydro-2,3?-bipyridine, (anatabine 6) N-(prop-2-en-1-yl)-1-(pyridin-3-yl)but-3-en-1-amine (5) (58.0 mg, 0.31 mmol) was dissolved in anhydrous CH2Cl2 (3 mL). p-Toluenesulfonic acid monohydrate (118 mg, 0.62 mmol) was added and the mixture was stirred for 10 min. Grubbs’ second-generation catalyst (NHC)(PCy3)Cl2Ru = CHR (25.5 mg, 0.030 mmol, 10 mol %) was added and the resulting mixture was stirred at room temperature for 18 h. The solvent was evaporated and the residue dissolved in EtOAc (30 mL) and 1 M HCl (10 mL) and the phases were separated. The organic layer was extracted additionally with 1 M HCl (3 × 10 mL). The combined aqueous layers were made alkaline (pH = 14) by adding NaOH(s). The basic solution was extracted with EtOAc (4 × 10 mL). The organic layers were combined, dried over anhydrous Na2SO4, filtered and concentrated to yield the crude product that was first stirred with activated carbon and then purified by flash chromatography (eluent: EtOAc:MeOH 95:5 + 1% Et3N, neutral alumina) yielding anatabine (29.8 mg, 0.19 mmol, 60%) as a yellow oil. Rf = 0.51 (EtOAc:MeOH 95:5 + 1% Et3N). 1H NMR (600.13 MHz, CDCl3, 25 °C): δ = 8.62 (dd, Jo',m = 0.8 Hz, Jo',p = 2.3 Hz, 1 H, Ho'), 8.52 (dd, Jo,p = 1.7 Hz, Jo,m = 4.8 Hz, 1 H, Ho), 7.74 (ddd, Jp,o = 1.7 Hz, Jp,o' = 2.3 Hz, Jp,m = 7.9 Hz, 1 H, Hp), 7.27 (ddd, Jm,o' = 0.8 Hz, Jm,o = 4.8 Hz, Jm,p = 7.9 Hz, 1 H, Hm), 5.87 (ddddd, JCH, CH2b' = -1.8 Hz, JCH,CH2b = 1.9 Hz, JCH,CH2a' = -2.4 Hz, JCH,CH2a = 5.6 Hz, JCH,CH' = 10.1 Hz, 1 H, CHCH'), 5.82 (ddddd, JCH',CH2a = -1.4 Hz, JCH',CH2a' = 2.0 Hz, JCH',CH2b = -2.7 Hz, JCH',CH2b' = 4.4 Hz, JCH,CH' = 10.1 Hz, 1 H, CHCH'), 3.90 (dd, JCH,CH2a = 3.8 Hz, JCH,CH2b = 10.4 Hz, 1 H, CH), 3.63 (ddddd, JCH2a', CH' = 2.0 Hz, JCH2a', CH = -2.4 Hz, JCH2a', CH2a = -3.2 Hz, JCH2a', CH2b = -4.3 Hz, JCH2a', CH2b' = -17.0 Hz, 1 H, NH-CH2a'-CH), 3.50 (ddddd, JCH2b',CH2a = -1.4 Hz, JCH2b', CH= = -1.8 Hz, JCH2b',CH2b = -2.5 Hz, JCH2b',CH' = 4.4 Hz, JCH2b',CH2a' = -17.0 Hz, 1 H, NH-CH2b'-CH), 2.27 (dddddd, JCH2b, CH = 1.9 Hz, JCH2b,CH2b' = -2.5 Hz, JCH2b, CH' = -2.7 Hz, JCH2b,CH2a' = -4.3 Hz, JCH2b,CH = 10.4 Hz, JCH2b,CH2a = -17.2 Hz, 1 H, CH-CH2b-CH), 2.26 (dddddd, JCH2a,CH' = -1.4 Hz, JCH2a,CH2b' = -1.4 Hz, JCH2a,CH2a' = -3.2 Hz, JCH2a,CH = 3.8 Hz, JCH2a,CH = 5.6 Hz, JCH2a,CH2b = -17.2 Hz, 1 H, CH-CH2a-CH) ppm. 13C NMR (150.9 MHz, CDCl3, 25 °C): δ = 148.8 (Co), 148.7 (Co'), 139.8 (Cm'), 134.1 (Cp), 126.2 (C'H), 125.1 (CH), 123.6 (Cm), 55.3 (CH), 46.0 (C'H2), 33.9 (CH2) ppm. HRMS calcd. for C10H13N2 [M+H]+: 161.1079, found: 161.1079.
	Multi-step reaction with 3 steps 1.1: potassium carbonate / 2-methyltetrahydrofuran / 24 h / 50 °C 2.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C 2.2: 3 h / 20 °C 3.1: trifluoroacetic acid / dichloromethane / 8 h / 0 °C
	Multi-step reaction with 4 steps 1.1: potassium carbonate / 2-methyltetrahydrofuran / 24 h / 50 °C 2.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C 2.2: 3 h / 20 °C 3.1: dichloromethane / 3 h / 20 °C 4.1: sodium hydroxide / tetrahydrofuran; water / 2 h / 20 °C

Reference： [1]Location in patent: experimental part Saloranta, Tiina; Leino, Reko [Tetrahedron Letters, 2011, vol. 52, # 36, p. 4619 - 4621]
[2]Rossi, Federico V.; Ballini, Roberto; Barboni, Luciano; Allegrini, Pietro; Palmieri, Alessandro [Synthesis, 2018, vol. 50, # 9, p. 1921 - 1925]
[3]Rossi, Federico V.; Ballini, Roberto; Barboni, Luciano; Allegrini, Pietro; Palmieri, Alessandro [Synthesis, 2018, vol. 50, # 9, p. 1921 - 1925]

18
1-(pyridin-3-yl)but-3-en-1-amine [ No CAS ]
[ 2743-90-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium hydroxide / N,N-dimethyl-formamide / 0.25 h / Inert atmosphere 1.2: 0.25 h / 20 °C / Inert atmosphere 2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; toluene-4-sulfonic acid / dichloromethane / 18 h / 20 °C / Inert atmosphere

Reference： [1]Saloranta, Tiina; Leino, Reko [Tetrahedron Letters, 2011, vol. 52, # 36, p. 4619 - 4621]

19
[ 87-69-4 ]
[ 2743-90-0 ]
anatabine L-(+)-tartrate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetone at 50℃; for 16h;	6 To a solution of anatabine (4.0 g, 24.9 mmol) in acetone (20 ml), L-(+)-tartaric acid (3.37, 22.4 mmol) was added at room temperature. The reaction mass was warmed to 50° C. for 16 hours. The supernatant was decanted and the solid was triturated with diethyl ether (20 ml), filtered and dried under vacuum.

Reference： [1]Current Patent Assignee: PHILIP MORRIS INTERNATIONAL INC. - US2011/237627, 2011, A1 Location in patent: Page/Page column 6

20
[ 77-92-9 ]
[ 2743-90-0 ]
anatabine citrate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetone at 50℃; for 16h; Inert atmosphere;	6 To a solution of anatabine (0.47 g, 2.9 mmol) in acetone (3 ml), citric acid (0.5 g, 2.6 mmol) was added at room temperature under a nitrogen atmosphere. The reaction mass was warmed to 50° C. for 16 hours. The supernatant was decanted and the solid was triturated with diethyl ether (20 ml), filtered and dried under vacuum.

Reference： [1]Current Patent Assignee: PHILIP MORRIS INTERNATIONAL INC. - US2011/237627, 2011, A1 Location in patent: Page/Page column 6

21
[ 500-22-1 ]
[ 2524-49-4 ]
[ 109720-72-1 ]
[ 2743-90-0 ]

Yield	Reaction Conditions	Operation in experiment
	With indium(III) triflate In dichloromethane at 80℃; for 15h; Inert atmosphere; Overall yield = 44 %;

Reference： [1]Colin, Olivier; Greck, Christine; Prim, Damien; Thomassigny, Christine [European Journal of Organic Chemistry, 2014, vol. 2014, # 31, p. 7000 - 7005]

22
tert-butyl 3,6-dihydro-[2,3'-bipyridine]-1(2H)-carboxylate [ No CAS ]
[ 2743-90-0 ]

Yield	Reaction Conditions	Operation in experiment
72%	With trifluoroacetic acid In dichloromethane at 0℃; for 8h;
420 g	With trifluoroacetic acid In dichloromethane Inert atmosphere; Cooling with ice;	2.4 (4) Preparation of the final product Weigh intermediate 3 (777.5g) placed in a 10L single-necked flask, protected by nitrogen, was added dichloromethane DCM5.0L stirring, ice salt bath, 2736.5g of trifluoroacetic acid was slowly added dropwise after completion of the dropwise addition, the reaction overnight.After completion of the reaction, spin the solvent, add water, ice salt bath, with saturated potassium hydroxide to adjust PH = 12, dichloromethane extraction 3 times; then the organic phase was washed with brine,Dried over anhydrous sodium sulfate, dried, and evacuated to give the final product 420g.

Reference： [1]Rossi, Federico V.; Ballini, Roberto; Barboni, Luciano; Allegrini, Pietro; Palmieri, Alessandro [Synthesis, 2018, vol. 50, # 9, p. 1921 - 1925]
[2]Current Patent Assignee: MAT X - CN107286132, 2017, A Location in patent: Paragraph 0021; 0029; 0030; 0038; 0039; 0047; 0048

23
[ 1476-11-5 ]
[ 175441-83-5 ]
[ 2743-90-0 ]

Yield	Reaction Conditions	Operation in experiment
17.3%	Stage #1: N-(diphenylmethylene)-1-(pyridin-3-yl)methanamine With lithium dipropan-2-ylazanide In tetrahydrofuran at -78 - -60℃; for 0.5h; Stage #2: (Z)-1,4-dichlorobut-2-ene In tetrahydrofuran at -60℃; for 1h;	2 3-(1,2,3,6-Tetrahydropyridin-2-yl)pyridine To a mixture of 1,1-diphenyl-N-(3- pyridylmethyl)methanimine (500 g, 1.84 mol) in tetrahydrofuran (1.00 L) was added lithium diisopropylamide (2 M, 1.00 L) at -78°C. After addition, the mixture was stirred at -60°C for 30 min. Then to the mixture was added cis-1 ,4-dichloro-2-butene (364 g, 2.91 mol, 305 mL) at -60°C. After addition, the mixture was stirred at -60 °C for 1 hr. The mixture was quenched with 2 N HCI (300 mL) and stirred at 25°C for 30 min. Then the mixture was extracted with methyl tert-butyl ether (500 mL x 3). Then the aqueous water phase was basified with solid K2CO3 to pH = 12. The water phase was stirred at 25°C for 2 hr. Then the water phase was extracted with dichloromethane (1 L x 5). The combined dichloromethane phases were washed with brine (2 L) and concentrated under reduced pressures to afford an oil residue. TLC (ethyl acetate - methanol = 10:1) showed a main new spot was found (Rf = 0.2). The oil was purified with chromatography column (silica gel, petroleum ether - ethyl acetate, 1:0 and ethyl acetate - methanol, 10:1, Rf = 0.2). Obtained crude material was purified with reverse chromatography (NH4ON, CH3CN) to give 3-( 1,2,3, 6-tetrahydropyridin- 2-yl)pyridine (52.0 g, 318 mmol, 17.3% yield, 98.1% purity); m/z (M+H)+ = 161; 1H NMR (400 MHz, CDCI3) d 8.55 (d, J = 2.0 Hz, 1H), 8.44 (dd, J = 1.6, 4.8 Hz, 1H), 7.66 (td, J = 1.6, 7.6 Hz, 1H), 7.30-7.11 (m, 1H), 5.89-5.60 (m, 2H), 3.83 (t, J = 7.2 Hz, 1H), 3.64-3.33 (m, 2H), 2.28-2.14 (m, 2H).
17.3%	Stage #1: N-(diphenylmethylene)-1-(pyridin-3-yl)methanamine With lithium dipropan-2-ylazanide In tetrahydrofuran at -78 - -60℃; for 0.5h; Stage #2: (Z)-1,4-dichlorobut-2-ene In tetrahydrofuran at -60℃; for 1h;	2 3-(1,2,3,6-Tetrahydropyridin-2-yl)pyridine To a mixture of 1,1-diphenyl-N-(3- pyridylmethyl)methanimine (500 g, 1.84 mol) in tetrahydrofuran (1.00 L) was added lithium diisopropylamide (2 M, 1.00 L) at -78°C. After addition, the mixture was stirred at -60°C for 30 min. Then to the mixture was added cis-1 ,4-dichloro-2-butene (364 g, 2.91 mol, 305 mL) at -60°C. After addition, the mixture was stirred at -60 °C for 1 hr. The mixture was quenched with 2 N HCI (300 mL) and stirred at 25°C for 30 min. Then the mixture was extracted with methyl tert-butyl ether (500 mL x 3). Then the aqueous water phase was basified with solid K2CO3 to pH = 12. The water phase was stirred at 25°C for 2 hr. Then the water phase was extracted with dichloromethane (1 L x 5). The combined dichloromethane phases were washed with brine (2 L) and concentrated under reduced pressures to afford an oil residue. TLC (ethyl acetate - methanol = 10:1) showed a main new spot was found (Rf = 0.2). The oil was purified with chromatography column (silica gel, petroleum ether - ethyl acetate, 1:0 and ethyl acetate - methanol, 10:1, Rf = 0.2). Obtained crude material was purified with reverse chromatography (NH4ON, CH3CN) to give 3-( 1,2,3, 6-tetrahydropyridin- 2-yl)pyridine (52.0 g, 318 mmol, 17.3% yield, 98.1% purity); m/z (M+H)+ = 161; 1H NMR (400 MHz, CDCI3) d 8.55 (d, J = 2.0 Hz, 1H), 8.44 (dd, J = 1.6, 4.8 Hz, 1H), 7.66 (td, J = 1.6, 7.6 Hz, 1H), 7.30-7.11 (m, 1H), 5.89-5.60 (m, 2H), 3.83 (t, J = 7.2 Hz, 1H), 3.64-3.33 (m, 2H), 2.28-2.14 (m, 2H).
	Stage #1: N-(diphenylmethylene)-1-(pyridin-3-yl)methanamine With lithium dipropan-2-ylazanide In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: (Z)-1,4-dichlorobut-2-ene In tetrahydrofuran at -45℃; for 8h; Inert atmosphere;	1.2 (2) Preparation of Intermediate 2 Weigh Intermediate 1 (544.7g) placed in 5L three-necked flask,Vacuum replaced nitrogen three times,Then add THF 2.5L;Start cooling and cooling to -78 ,Start slowly dropping LDA 900ml,After the addition is completed,Insulation reaction 30min.Then, naturally warming,When warmed to -45 ° C,250.0 g of cis 1,4-dichloro-2-butene was added dropwise.After the addition is completed,Warmed to room temperature,Stir 8h, TLC monitoring reaction was complete.After the reaction is completed,The reaction solution was poured into 1500ml 10% hydrochloric acid solution was quenched,Stirring 30min; ether extraction of impurities;With 40% potassium hydroxide solution to adjust PH = 12,Extract with chloroform (500 * 3)The organic phase is washed with brine,Dried over anhydrous sodium sulfate,Spin dry, purify by silica gel column (DCM: MeOH = 10: 1)Intermediate 2 was obtained.

Reference： [1]Current Patent Assignee: PHILIP MORRIS INTERNATIONAL INC. - WO2021/260029, 2021, A1 Location in patent: Page/Page column 55; 59; 64-65
[2]Current Patent Assignee: PHILIP MORRIS INTERNATIONAL INC. - WO2021/260029, 2021, A1 Location in patent: Page/Page column 55; 59; 64-65
[3]Current Patent Assignee: MAT X - CN107286132, 2017, A Location in patent: Paragraph 0021; 0025; 0026; 0034; 0035; 0043; 0044

24
[ 24424-99-5 ]
[ 2743-90-0 ]
tert-butyl 3,6-dihydro-[2,3'-bipyridine]-1(2H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate In tetrahydrofuran; water for 8h; Cooling with ice; Inert atmosphere;	2.3 (3) Preparation of Intermediate 3 Intermediate 2 (477.0 g) was weighed, 2.0 L of THF and 5 L of aqueous sodium carbonate were added; 654.8g of di-tert-butyl dicarbonate was added dropwise slowly under an ice bath; after the addition was completed, the reaction was protected by nitrogen for 8 hours.After the reaction was completed, the mixture was extracted with ethyl acetate three times. The organic phase was then washed with brine, dried over anhydrous sodium sulfate and dried to give 648.0 g of crude product.The residue was purified by silica gel column chromatography (PE: EA = 5: 1) to give Intermediate 3.

Reference： [1]Current Patent Assignee: MAT X - CN107286132, 2017, A Location in patent: Paragraph 0021; 0027; 0028; 0036; 0037; 0045; 0046

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[ CAS No. 2743-90-0 ]

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[ 2743-90-0 ] Synthesis Path-Downstream 1~24

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