Day: March 18, 2022

Application of 357927-50-5, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.357927-50-5, name is 2-Bromo-4-fluoropyridine, molecular formula is C5H3BrFN, molecular weight is 175.99, as common compound, the synthetic route is as follows.

Under the argon atmosphere, 3 g of 2-bromo-4-fluoropyridine was added to 35 ml of tetrahydrofuran, and 9.38 ml of lithium diisopropylamide (2 mol/1 heptane/tetrahydrofuran/ethylbenzene solution) was added at -780C. After stirring for 2 hours, 5.66 g of iodine was added, and the mixture was further stirred for 4 hours. The reaction solution was poured into an aqueous saturated sodium thiosulfate solution, the resultant solution was extracted with tert-butyl=methyl=ether three times, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 4.1 g of 2-bromo-5-fluoro-4-iodopyridine. 2-Bromo-5-fluoro-4-iodopyridine.1H-NMR: 7.91 (d, IH), 8.13 (s, IH)

Statistics shows that 357927-50-5 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-4-fluoropyridine.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2009/66786; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1020635-54-4, name is 2-Methoxy-5-nitronicotinic acid, molecular formula is C7H6N2O5, molecular weight is 198.13, as common compound, the synthetic route is as follows.HPLC of Formula: C7H6N2O5

2-Methoxy-5-nitro-nicotinic acid (36 mmol) and phosphorous pentachloride (72 mmol) were heated at 100 0C for 2h, The excess reagent was removed in vacuo to give an oily residue.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1020635-54-4, 2-Methoxy-5-nitronicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; BIONOMICS LIMITED; WO2008/46135; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 3430-21-5, 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 3430-21-5, name is 5-Bromo-3-methylpyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

To dioxane (10 mL) was added 5-bromo-3-methylpyridin-2-amine (2 g, 10.6 mmol), sodium iodide (3.2 g, 21.4 mmoL), copper iodide (0.190 g, 1.06 mmol) and the solution degassed followed by addition of tetramethylethane-1,2-diamine (0.803 mL, 1.06 mmol) this mixture heated at 110 C. overnight. After cooling water was added and extracted the crude product with ethyl acetate. The residue was purified by column chromatography to give 5-iodo-3-methylpyridin-2-amine as a beige solid (2.3 g, 93%). Analogous to the procedure described in Ex. 40, 6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-one (0.100 g, 0.51 mmol) and 5-iodo-3-methylpyridin-2-amine (0.119 g, 0.53 mmol) were coupled to yield pure 3-(6-aminopyridin-3-yl)-6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-one (0.020 g, 13%) after reverse phase HPLC purification. ES-MS (M+H)+=303. Analogous to the sulfonylurea urea formation described in Ex 5, 3-(6-amino-5-methylpyridin-3-yl)-6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-one (0.010 g, 0.034 mmol) and (5-Chloro-thiophene-2-sulfonyl)-carbamic acid ethyl ester (0.048 g, 0.166 mmol) were coupled to give 1-(5-chlorothiophen-2-ylsulfonyl)-3-(5-(6-fluoro-7-(methylamino)-4-oxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)-3-methylpyridin-2-yl)urea (0.016 g, 85%). RP-HPLC: 2.7 min; ES-MS (M+H)+=526.0; 1H-NMR (DMSO-d6) delta (ppm): 2.2 (s, 3), 2.8 (s, 3), 5.6 (s, 2), 6.2 (d, 1), 6.8 (bs, 1), 7.2 (s, 1), 7.4 (d, 1), 7.6 (s, 1), 7.8 (d, 1), 8.2 (d, 1), 9.6 (bs, 1).

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 3430-21-5, 5-Bromo-3-methylpyridin-2-amine.

Reference:
Patent; Portola Pharmaceuticals, Inc.; US2006/69093; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 98197-88-7, 2-(Hydroxymethyl)-4-nitropyridine, 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, Computed Properties of C6H6N2O3, blongs to pyridine-derivatives compound. Computed Properties of C6H6N2O3

To a stirred solution of (4-nitro-pyridin-2-yl)-methanol (1000 mg; 6.42 mmol) in dichloromethane (30 mL) was gradually added phosphorus tribromide (0.79 mL; 8.35 mmol) at 0 C. After addition, the mixture was heated to reflux for 3 hours. The reaction mixture was then cooled to 0 C and cautiously deactivated with water. A saturated aqueous solution of potassium carbonate was cautiously added to the mixture until basic pH. The organic layer was separated and washed with brine, dried over Na2S04 and then concentrated to dryness to afford crude 2-(bromomethyl)-4-nitro-pyridine (1400 mg) as a brown oil, directly used in the next step without further purification. MS m/z (+ESI): 216.9, 219.0 [M+H]+.

The synthetic route of 98197-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASILEA PHARMACEUTICA INTERNATIONAL AG; LANE, Heidi; RICHALET, Florian; EL SHEMERLY, Mahmoud; (169 pag.)WO2018/2220; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 213193-32-9, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.213193-32-9, name is 5-Acetyl-2-methoxypyridine, molecular formula is C8H9NO2, molecular weight is 151.16, as common compound, the synthetic route is as follows.

[0560] To a solution of III-2 (5 g, 33 mmol) in 20 mL of EtOH was added aq. HBr (48%, 60 mL), the reaction mixture was heated to reflux overnight. After being cooled to rt., the mixture was neutralized by addition of saturated aq. NaHCO3, extracted with EtOAc (100 mL×3). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated to supply crude III-3 (3 g, 65% yield) as white solid.

The chemical industry reduces the impact on the environment during synthesis 213193-32-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Buckman, Brad Owen; Nicholas, John Beamond; Ramphal, Johnnie Y.; Emayan, Kumaraswamy; Seiwert, Scott D.; US2014/94456; (2014); 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

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

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

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

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