Category: pyridine-derivatives

Electric Literature of 7471-05-8 ,Some common heterocyclic compound, 7471-05-8, molecular formula is C8H9N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

General procedure for dehydrogenation of imidazolines with NaIO4 catalyzed by [Mn(TPP)Cl]: All of the reactions were carried out at room temperature under air in a 25 mL flask equipped with a magnetic stirrer bar. A solution of NaIO4 (2 mmol) in H2O (10 mL) was added to a mixture of 2-imidazolines (1 mmol), [Mn(TPP)Cl] (0.05 mmol) in CH3CN (5 mL). The progress of reaction was monitored by TLC (eluent: EtOAc/MeOH 4:1). After the reaction was completed, water (30 mL) was added and the corresponding imidazoles were extracted with CH2Cl2 (2 x 20 mL). The imidazole derivatives were obtained after evaporation of solvent. IR and 1H NMR spectral data confirmed the identities of the products.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 7471-05-8, 2-(4,5-Dihydro-1H-imidazol-2-yl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kargar, Hadi; Moghadam, Majid; Mirkhani, Valiollah; Tangestaninejad, Shahram; Mohammadpoor-Baltork, Iraj; Nameni, Iman; Bioorganic and Medicinal Chemistry Letters; vol. 21; 7; (2011); p. 2146 – 2148;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 628691-93-0 ,Some common heterocyclic compound, 628691-93-0, molecular formula is C6H3ClFNO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

.-Benzyl-6-chloro-7-fluoro- 1 H-spiro [furo [3 ,4-c]pyridine-3 ,4′ -piperidin] – 1 -one2 3To a solution of 2,2,6,6-tetramethylpiperidine (72 g, 0.51 mol) in 200 ml of anhydrous THF under nitrogen at -78C was added n-BuLi (270 ml, 0.68 mol). After stirring for 0.5 h, the resulting mixture was added to a solution of 2-ch]oro-3-fluoropyridine-4-carboxylic acid (35 g, 0.2 mol) in 80 ml of anhydrous THF under nitrogen at -78C. After stirring for 3 h, the reaction mixture was added a solution of l-benzyl-piperidin-4-one (38 g, 0.20 mol) in 50 ml of THF under nitrogen at -78C. After stirring at -78C for 2 h, and room temperature for 1 h5 the reaction was quenched with 2 M aqueous hydrochloride (final pH = ca 2). The mixture was stirred at room temperature overnight, and the pH was adjusted to 9-10 with 2 M aq sodium hydroxide. The product was extracted with ethyl acetate (3x 500 mL), and the combined extracts were washed with brine, dried over Na2S0 j filtered and concentrated. The residue was purified by eluting on a silica gel column with PE: EtOAc = 3:1 to give the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,628691-93-0, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD K.K.; LIN, Linus, S.; SUZUKI, Takao; WO2011/37771; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 25194-01-8 ,Some common heterocyclic compound, 25194-01-8, molecular formula is C5H2Cl2N2O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Step A: 4,6-dichloro-1 H-pyrrolor3,2-clpyridine: 2,6-dichloro-4-nitro-pyridine (1 1 g, 57 mmol) was dissolved in dry tetrahydrofurane (300 ml_), cooled to -78C and treated dropwise with bromo(vinyl)magnesium (1 M in THF, 200 ml_, 200 mmol). The reaction was allowed to react at this temperature for 1 hour and then allowed to warm to -20C. The reaction mixture was then quenched with 200 ml of aqueous NH4CI and the mixture obtained was partitioned in ethyl acetate. The aqueous layer was extracted 3 times with 200 ml of ethyl acetate and the combined organic layer dried over Na2S04, filtered and concentrated in vacuo. Purification by Combi flash chromatography with a column of 120g and a gradient cyclohexane:0-100% ethyl acetate, and then with a column of 40 g and a gradient dichloromethane:0-10% ethyl acetate gave the title compound as brown solid (0.150 g, 1 .4%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,25194-01-8, its application will become more common.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; EDMUNDS, Andrew; BIGOT, Aurelien; HALL, Roger Graham; JEANGUENAT, Andre; LUKSCH, Torsten; RENDLER, Sebastian; WO2013/156431; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1195189-83-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1195189-83-3, name is 2-Chloro-3-methylisonicotinonitrile, molecular formula is C7H5ClN2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

In a pre-dried flask, Dl (12.6 g; 82.9 mmol) was dissolved in Et2O (anhydrous) (200 ml) and under N2 (gas) protection, bro mo methyl magnesium (100 ml) was added slowly. The reaction mixture was stirred at room temperature overnight and then poured slowly into a mixture of ice-H2O (600 ml) and 37% aqueous HCl (100 ml). The reaction mixture was stirred and extracted with Et2O (200 ml x 4). The combined organic phases were then washed with brine, dried (Na2SO4), filtered and the solvent evaporated in vacuo. Yield: 11.6 g of D2 (88 % pure product).

According to the analysis of related databases, 1195189-83-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WO2009/135944; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 127406-55-7, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 127406-55-7, name is 4-Pyridin-3-yl-benzaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Step 1F 1-(7-Azabicyclo[2.2.1]hept-7-yl)-2-{2-(3,5-dimethylphenyl)-3-[2-(4-pyridin-3-yl-benzylamino)ethyl]-1H-indol-5-yl}-2-methylpropan-1-one To a solution of 2-[3-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-1-(7-azabicyclo[2.2.1]hept-7-yl)-2-methyl-propan-1-one (20 mg in 1.5 mL dry, degassed tetrahydrofuran) was added 9.4 mg 4-pyridin-3-yl-benzaldehyde followed by 43 mg titanium (IV) isopropoxide and the mixture stirred at room temperature. After 60 hours, the reaction was cooled to 0 C. and a solution of sodium cyanoborohydride (9.0 mg in 0.50 mL methanol) was added along with 0.026 mL acetic acid and the mixture stirred at low temperature. The reaction was quenched after 45 minutes by the addition of saturated aqueous ammonium chloride and brine. This was then extracted with ethyl acetate and the organics washed with brine, dried over magnesium sulfate and concentrated in vacuo. Purification of the residue by flash chomatography on silica gel (ethyl acetate:hexane, 75:25; then methylene chloride:10% ammonium hydroxide in methanol, 98:2; then 97:3; then 95:5) gave the title compound (8.0 mg). MASS: 597 (M+H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 127406-55-7, 4-Pyridin-3-yl-benzaldehyde.

Reference:
Patent; Merck & Co., Inc.; US5985901; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1018505-59-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1018505-59-3, name is 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine, molecular formula is C11H18N4, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Add to the reaction flask7- (2-chloro)Fluoro-pyrimidin-4-yl) -5-fluoro-2,3-dihydro-1H-benzo [d]Pyrrole [1,2-a] imidazole(200 mg, 0.6 mmol, prepared according to the procedure of Example 1)5- (4-ethylpiperazin-1-yl) pyridin-2-amine (123 mg, 0.6 mmol, prepared in second step)Cesium carbonate (390 mg, 1.2 mmol), Pd2 (dba) 3 (55 mg, 0.06 mmol)XantPhos (35 mg, 0.06 mmol) and anhydrous 1,4-dioxane (5 mL).The mixture was stirred at 120 C for 12 hours.Cooled to room temperature, water (10 mL) and ethyl acetate (20 mL x 3) were added to the solution.The combined organic phases were washed with saturated sodium chloride solution (20 mL), dried over anhydrous sodium sulfate,Filtered, concentrated under reduced pressure. The residue was purified by column chromatography (DCM / MeOH = 10: 1)The resulting residue was purified to give the title compound (50 mg, white solid)Yield 17%.

According to the analysis of related databases, 1018505-59-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gan & Lee Pharmaceuticals; Liu, Wenjian; Yin, Lei; Li, Heng; (94 pag.)CN106608879; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1018505-59-3, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 1018505-59-3, name is 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

A reaction flask was charged with 321 mg (1 mmol) of 5-(2-chloro-5-fluoropyrimidin-4-yl)-3-ethyl-7-fluoro-2,3-dimethyl-3H-indole prepared in Step 3, 206 mg (1 mmol) of 5-(4-ethylpiperazin-1-yl)pyridin-2-amino obtained in Step 2, 2 ml of 1,4-dioxane, 650 mg (2 mmol) of Cs2CO3, 91mg (0.1mmol) of Pd2(dba)3, and 58mg (0.1mmol) of diphenylphosphine. The mixture was heated to 120C to conduct microwave reaction for 1 h. The reaction product was cooled to room temperature, added with 10ml of water and then extracted with ethyl acetate three times (40ml for each time). The organic phases were combined, washed once with 40 ml of saturated salt solution, dried with sodium sulfate, filtered, concentrated under reduced pressure and separated by silica gel column chromatography (DCM/MeOH = 10:1) to give the titled compound (49 mg, yellow solid), yield 10%. 1H-NMR(400MHz, CDCl3) delta9.25(br s, 1H), 8.46(d, 1H, J=3.2Hz), 8.28(d, 1H, J=9.2Hz), 8.17(d, 1H, J=2.0Hz), 7.90(d, 1H, J=11.2Hz), 7.82(s, 1H), 7.35(dd, 1H, J=9.2Hz, 2.8Hz), 3.20-3.18(m, 4H), 2.64-2.61(m, 4H), 2.51(q, 2H, J=6.8Hz), 2.31(s, 3H), 2.03-1.94(m, 1H), 1.89-1.82(m, 1H), 1.36(s, 3H), 1.13(t, 3H, J=7.2Hz), 0.48(t, 3H, J=7.2Hz). MS(ESI):m/z 492.3[M+H]+.

According to the analysis of related databases, 1018505-59-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gan & Lee Pharmaceuticals; YIN, Lei; LIU, Wenjian; LI, Heng; ZHU, Dianxi; (73 pag.)EP3385262; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 60186-15-4 , The common heterocyclic compound, 60186-15-4, name is 2,4-Difluoro-5-nitropyridine, molecular formula is C5H2F2N2O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

In a 50 mL round-bottomed flask vial was 2,4-difluoro-5-nitropyridine (263.4 mg, 1.645 mmol) in tetrahydrofuran (8 mL) to give a tan solution. After cooling to -40 C, 2-vinylmorpholine hydrochloride (246 mg, 1.645 mmol) was added, followed by Et3N (0.688 mL, 4.94 mmol). The cloudy tan mixture was stirred at -40 C – 0C for 5 h. TLC (1/2 EtOAc/hexane) showed little SM and one major more polar spot. The mixture was concentrated, and the residue was purified by FCC up to 60% EtOAc/hexane to afford the desired product (348 mg, 84%) as a yellow oil: 1H NMR (400 MHz, Chloroform-d) delta 8.55 (s, 1H), 6.44 (s, 1H), 6.03 – 5.88 (m, 1H), 5.38 – 5.28 (m, 1H), 5.28 – 5.17 (m, 1H), 3.98 – 3.85 (m, 4H), 3.80 (ddd, J = (0086) 11.4, 10.6, 2.8 Hz, 1H), 3.53 (ddd, J = 12.8, 10.6, 3.5 Hz, 1H), 2.95 (dtd, J = 12.9, 2.6, 0.9 Hz, 1H); 19F NMR (376 MHz, Chloroform-d) delta -61.65.

The synthetic route of 60186-15-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LUO, Guanglin; SIVAPRAKASAM, Prasanna; DUBOWCHIK, Gene M.; MACOR, John E.; (45 pag.)WO2018/98413; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 936841-69-9, 4-(Trifluoromethyl)picolinonitrile, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 936841-69-9, blongs to pyridine-derivatives compound. Computed Properties of C7H3F3N2

To 4-trifluoromemyl-2-pyridinecarbonitrile (262 mg, 1.52 mmol) was added a solution of sodium methoxide in methanol (0.1 M, 1.5 ml, 0.1 eq.) and the solution heated under nitrogen in a 40-45 C oil-bath for 105 min. A solution of 2-amino-4-(5′-(4″- methylpiperazin- 1 “-yl)benzimida7ol-2′-yl)aniline (295 mg, 0.92 mmol) in dry methanol (15 ml) and glacial acetic acid (0.18 ml, 3.1 mmol) was then added and the mixture gently refluxed under nitrogen for 19 h. After cooling the solvents were removed by rotary evaporator, the residue dissolved in water (10 ml) and basified to pH 8 with dilute ammonia solution (3.0 M). The oily precipitate was stirred for 40 min to give a friable light brown suspension that was centrifuged and the supernatant removed. Then solid was then treated with water (3 x 8 ml), followed by acetonitrile (3 x 4 ml) with centrifuging and removal of the supernatant between treatments. The remaining solid was dried under vacuum to give a dull yellow powder (358 mg). A portion of this material (250 mg) was dissolved in methanol (1-2 ml) and applied to a silica cartridge (KP-Sil 25g) and eluted with methanol to give 2-(5 ‘-(5”-(4’ ‘ ‘-methylpiperazin- 1 ‘ “-yl)ben/imidayol-2″- yl)benzimidaz»l-2’-yl)-4-(trifluoromemyl)pyridine as a yellow powder (236 mg, 77%), mp 203-208 C. nmr (400 MHz, dj-MeOH + 5 drops d-TFA) delta 3.01, s, 3H, 4″‘-MeN; 3.21, t (J =12.0 Hz), 2H, NCH2; 3.35, m (obs), NCH2; 3.68, d ( J = 12.0 Hz), 2H, NCH2; 3.96, d (J = 13.6 Hz), 2H, NCH2; 7.32, d (J = 2.0 Hz), 1H, H4″; 7.41, dd (J = 2.5, 9.2 Hz), 1H, H6″; 7.73, d (J = 8.8 Hz), 1H, H7″; 7.88, m, 1H, H5; 8.01, dd (J = 0.6, 8.6 Hz), 1H, H7′; 8.09, dd (J = 2.5, 8.8 Hz), 1H, H6′; 8.52, m, 1H, H4’; 8.66, s, 1H, H3; 9.05, d (J = 4.8 Hz), 1H, H6. ,3C nmr (125 MHz, dj-MeOH + 5 drops HOAc) delta 43.6, 4″‘-MeN; 49.4, C2″76″‘; 54.7, C3″75′”; 102.7, C4″; 115.4, 116.4, 116.8, 117.1, C4 C6″, C7 CT; 118.0, 121.2, C3, C5; 123.4, C6’; 124.1, q (‘JCF = 273 Hz), 4-F3C; 124.9, C5′; 134.6, C7a”; 139.2, C3a’ or C3a”; 140.3, d (2JCF = 34 Hz), C4; 140.5, C3a” or C3a’; 141.4, C7a’; 148.5, C5″; 150.2, C2; 152.2, C6; 152.7, 152.9, C2 C2″. MS (ESI +ve) m/z 478 (MH+, 100%). HRMS (ESI +ve) m/z 478.19599, C25H23F3N7 requires 478.19615 (Delta = 0.3 ppm).Cytotoxicity and radioprotection resultsC50 = 23.3PF = 63.8DMFm = 2.75DMF10 = 2.58

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,936841-69-9, its application will become more common.

Reference:
Patent; PETER MACCALLUM CANCER INSTITUTE; MARTIN, Roger, Francis; WHITE, Jonathan; LOBACHEVSKY, Pavel; WINKLER, David; SKENE, Colin; MARCUCCIO, Sebastian; WO2011/123890; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 628691-93-0 , The common heterocyclic compound, 628691-93-0, name is 2-Chloro-3-fluoroisonicotinic acid, molecular formula is C6H3ClFNO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

A mixture of lithium diisopropylamide (2M in heptane/ tetrahydrofuran/ethylbenzene-stabilised with magnesium bis- (diisopropylamide), 16. 7 ml) and tetrahydrofuran (30 ml) was cooled to [- 78C] and [A PRE-COOLED (-78C)] solution of 2-chloro-3-fluoropyridine (4.0 g, 30.4 mmol) in tetrahydrofuran (30 ml) was added dropwise over 20 min. After 3 h, carbon dioxide was bubbled through the cold reaction mixture for 20 min. The reaction was then warmed [TO-30C] for 1 h then warmed [TO 0C.] The mixture was quenched by the addition of water (75 [ML).] The aqueous phase was washed with diethyl ether (100 ml), then the pH of the solution adjusted to 2 by the addition of 2N hydrochloric acid. The resulting white precipitate was aged for 18 h then filtered and left to air- dry, which afforded [2-CHLORO-3-FLUOROISONICOTINIC] acid as a white solid (4.22 g, 79%): 8H (360 MHz, DMSO) 7. 80 [(1H,] dd, J 5 and 5), 8. 39 [(1H,] d, J 5), 14.20 [(1H,] s). [2-CHLORO-3-FLUOROISONICOTINIC] acid (3.30 g, 18.8 mmol) was suspended in thionyl chloride (40 ml) and heated under reflux for 2.5 h. The solvent was evaporated and the residue dried by means of azeotropic removal of water with toluene (100 ml) to afford a pale yellow oil. The oil was dissolved in dichloromethane (20 ml) and cooled to 0C before methanol (2.42 g, 75.3 mmol) was added dropwise to the solution over 15 min. On complete addition the mixture was allowed to warm to ambient temperature and stirred for [18] h. The solvent was evaporated and the mixture partitioned between water (75 ml) and dichloromethane (100 ml). The aqueous phase was extracted further with dichloromethane (100 ml), the organic layers were combined, washed with brine (75 ml), dried over anhydrous sodium sulphate, filtered and evaporated to give 2-chloro-3- fluoroisonicotinic acid methyl ester (3.32 g, 93%) as a pale yellow solid: [SN] (360 MHz, [CDCL3)] 3.99 (3H, s), 7.70 [(1H,] dd, J 5 and 5), 8. 31 [(1H,] d, J 5). [2-CHLORO-3-FLUOROISONICOTINIC] acid methyl ester (3.32 g, 17.5 mmol) was converted to 8-fluoroimidazo [[L,] 2-a] pyridine-7-carboxylic acid methyl ester (1.4 g, 41%) as described in Example 1. [8-FLUOROIMIDAZO] [1, 2-a] [PYRIDINE-7-CARBOXYLIC] acid methyl ester (0.19 g, 1.0 mmol) was brominated as described in Example [1,] affording 3- [BROMO-8-FLUOROIMIDAZO] [1, 2-a] pyridine-7-carboxylic acid methyl ester (195 mg, 71%): [8H] (360 MHz, CDCl3) 4.00 (3H, s), 7. 32 [(1H,] t, [J 6.] 9), 7.43 (1H, dd, [J 7] and 6), 8. 19 [(1H,] s), 8. 37 [(1H,] d, [J 7).] 3-Bromo-8-fluoroimidazo [[L,] 2-a] pyridine-7-carboxylic acid methyl ester (0.10 g, 0.37 mmol) and 4, [2′-DIFLUORO-5′- (5,] 5-dimethyl- [1, 3,2] [DIOXABORINAN-2-YL) BIPHENYL-2-CARBONITRILE] (0.15 g, 0.44 mmol) were coupled following the procedure in Example 1 to afford 3- (2′-cyano-2, 4′- difluorobiphenyl-5-yl) -8-fluoroimidazo [1, 2-a] pyridine-7-carboxylic acid methyl ester (79 mg, 53%) as a white solid: [6H] (400 MHz, CDCl3) 4.00 (3H, s), 7.35 [(1H,] dd, J 7 and 7), 7.34-7. 46 (2H, [M), 7. 53-7.] 66 (4H, m), 7.85 (1H, [S),] 8. 24 [(1H,] [D,] J [7)] ; m/z [(ES+)] 408 [(100%,] [MHZ+).]

The synthetic route of 628691-93-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2003/99816; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem