Day: March 24, 2022

Reference of 1235036-15-3 ,Some common heterocyclic compound, 1235036-15-3, molecular formula is C10H11BrClNO2, 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.

To Example 1.1.10 (100 mg) and tert-butyl 3-bromo-6-chloropicolinate (52.5 mg) in dioxane (2 mL) was added tris(dibenzylideneacetone)dipalladium(0) (8.2 mg), K3P04 (114 mg), 1,3,5,7- tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphaadamantane (5.24 mg) and water (0.8 mL). The mixture was stirred at 95 C for 4 hours, diluted with ethyl acetate and washed with water and brine. The organic layer was dried over Na2S04, filtered, concentrated and purified by flash chromatography, eluting with 20% ethyl acetate in heptanes and then with 5% methanol in dichloromethane, to provide the title compound. MS (ESI) m/e 643.3 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1235036-15-3, its application will become more common.

Reference:
Patent; ABBVIE INC.; BENATUIL, Lorenzo; BRUNCKO, Milan; JUDD, Andrew, S.; LI, Yingchun; MCCLUSKEY, Andrew; PHILLIPS, Andrew, C.; PHILLIPS, Darren, C.; SEAGAL, Jane; SOUERS, Andrew, J.; (608 pag.)WO2017/214458; (2017); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1092286-30-0, 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 1092286-30-0, name is 5-Chloro-2-methyl-3-pyridinecarboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

Step 1 : 5-Chloro-2-methylnicotinoyl chloride5-Chloro-2-methyl-nicotinic acid (4.15 g, 24.2 mmol) was placed in a flask with DCM (100 ml) and oxalyl chloride (3.68 g, 29 mmol). DMF (200 muIota) was added and the reaction mixture was stirred at RT for 1 hour (gas evolution). The mixture was filtered and the solvent was removed in vacuo to afford the title product which was used in the next step without further purification.

According to the analysis of related databases, 1092286-30-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ATKINSON Benjamin; BEATTIE David; CULSHAW Andrew James; DEVEREUX Nicholas James; MCKENNA Jeffrey; DALE James; WO2011/92293; A1; (2011);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 868551-30-8, name is Methyl 4-methyl-5-nitropicolinate. A new synthetic method of this compound is introduced below., Computed Properties of C8H8N2O4

A mixture of methyl 4-methyl-5-nitropyridine-2-carboxylate (39.5g, 0.19mol) and DMF- DMA (30.6 g, 0.26mol, 1.35 eq) in DMF (470 mL) was heated to 90C for 30 min. The solvent was removed in vacuo. The residue (78g) was used without further purification in the next step.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 868551-30-8, Methyl 4-methyl-5-nitropicolinate.

Reference:
Patent; PFIZER INC.; WO2005/103003; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 89510-90-7, name is 2-Chloro-5-fluoro-4-pyridinamine, molecular formula is C5H4ClFN2, 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. Formula: C5H4ClFN2

2-(5-chloro-2-methoxy-phenyl)acetic acid (753 mg, 3.75 mmol) in thionyl 1 mL, 68.24 mmol) was stirred at 70 C for 1 hour. The resulting mixture was to dryness and azeotroped with toluene (2 x 10 mL). The crude residue was DMF (10 mL) and treated dropwise with a solution of 2-chloro-5-fluoro-pyridin- 0 mg, 3.41 mmol) in DMF (3 mL) followed by DIPEA (1.49 mL, 8.53 mmol). at room temperature under an inert atmosphere for 16 hours, the mixture was tOAc (100 mL) and washed with water (2 x 50 mL) and brine (2 x50 mL). The on was dried over Na2SO4 and concentrated in vacuo. The crude material was 18 reverse phase chromatography eluting with 0-100% MeCN in water with acid modifier to afford the titled compound as a light yellow solid. 0 MHz, DMSO-d6) delta 10.58 (s, 1H), 8.41 (d, J = 2.7 Hz, 1H), 8.24 (d, J = 5.6 3-7.28 (m, 2H), 7.01 (d, J = 9.5 Hz, 1H), 3.83 (s, 2H), 3.75 (s, 3H). hod E): Rt 1.25 mins; MS m/z 328.9, 330.9= [M+H]+

With the rapid development of chemical substances, we look forward to future research findings about 89510-90-7.

Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; COLLINGWOOD, Stephen; MCCARTHY, Clive; HARGRAVE, Jonathan, David; HAY, Duncan, Alexander; SCHOFIELD, Thomas, Beauregard; ELLAM, Sarah; BUXTON, Craig; HABGOOD, Matthew; INGRAM, Peter; MA, Chun Yan; NAPIER, Spencer; SHAIKH, Abdul; SMITH, Matthew; STIMSON, Christopher; WALKER, Edward; (401 pag.)WO2019/145726; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 90993-26-3, Adding some certain compound to certain chemical reactions, such as: 90993-26-3, name is 7-Bromo-1H-imidazo[4,5-c]pyridine,molecular formula is C6H4BrN3, 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 90993-26-3.

Step 3: 7-bromo-l-((2-(trimethylsilyl)ethoxy)methyl)-lH-imidazo[4,5-c]pyridine 5-oxide To a stirred solution of 7-bromo-lH-imidazo[4,5-c]pyridine 5-oxide (425 mg, 1.99 mmol) and N,N- dimethylformaldehyde (5.5 mL) at 0 C was added N,N-diisopropylethylamine (1.05 mL, 5.96 mmol), tetrabutylammonium iodide (74 mg, 0.199 mmol) and 2-(trimethylsilyl)ethoxymethyl chloride (0.78 mL, 3.97 mmol) and the reaction mixture stirred for 30 min at RT. The reaction mixture was washed with water (10 mL) and extracted with dichloromethane (2 x 10 mL). The combined organic layers were dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 0 to 10% methanol in dichloromethane) affording an approximate 3:2 mixture of 7-bromo-l-((2- (trimethylsilyl)ethoxy)methyl)-lH-imidazo[4,5-c]pyridine 5-oxide and 7-bromo-3-((2- (trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-c]pyridine 5-oxide N-(2- (trimethylsilyl)ethoxy)methane regioisomers as an orange foam (580 mg, 54%): H NMR (400 MHz, DMSO-d6; reported as an approximate 3:2 mixture of N-(2-(trimethylsilyl)ethoxy)methane isomers) delta 8.73 (d, = 1.5 Hz, 0.6 H), 8.60 (d, = 1.6 Hz, 1H), 8.38 (d, = 1.5 Hz, 1H), 8.36 (d, = 1.5 Hz, 0.6H), 8.10 (s, 1H), 8.09 (s, 0.6H), 5.76 (s, 1.3H), 5.48 (s, 2H), 3.63 – 3.59 (m, 1.4H), 3.56 – 3.50 (m, 2H), 0.97 – 0.91 (m, 3H), -0.01 (s, 9H), -0.02 (s, 6H).

According to the analysis of related databases, 90993-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; HUESTIS, Malcolm; KELLAR, Terry; PATEL, Snahel; SHORE, Daniel; SIU, Michael; (260 pag.)WO2016/142310; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 175204-82-7, Methyl 4-(trifluoromethyl)nicotinate, 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 C8H6F3NO2, blongs to pyridine-derivatives compound. Computed Properties of C8H6F3NO2

Step 1. To a stirred suspension of LAH (0.64 g, 17.0 mmol) in THF (30 mL) at -78 C. was added dropwise methyl 4-trifluoromethylnicotinate (1.74 g, 8.48 mmol) in THF (20 mL). The mixture was stirred for 1 h then carefully quenched with aqueous NaHCO3 (80 mL) and extracted with CH2 Cl2 (3*100 mL). The combined organic extracts were dried (Na2 SO4) and concentrated in vacuo to give 3-hydroxymethyl-4-trifluoromethylpyridine as an oil (TLC: Rf = 0.35 (1:1 hexane:EtOAc)).

The synthetic route of 175204-82-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5756497; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 60753-14-2 , The common heterocyclic compound, 60753-14-2, name is 4-(Pyridin-3-yl)butan-1-ol, molecular formula is C9H13NO, 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) N-(3-Nicotinylpropyl)benzylamine To a solution of 3-nicotinyl-1-propanol (50.0 g, 365 mmol) and triethylamine (110 g, 1.09 mol) in methylene chloride (500 ml) at 0 C. was added dropwise methanesulfonyl chloride (83.5 g, 7.29 mmol). The solution was stirred at 0 C. for 1 hour and then RT for 1 hour, and the excess of methanesulfonyl chloride was carefully decomposed with ice-water. The organic layer was separated and washed with water (twice). The aqueous layer and washings were combined, basified with 50% aqueous sodium hydroxide, and extracted with methylene chloride (3 times). The methylene chloride extracts were combined, washed with saturated brine solution, dried (MgSO4), and evaporated to give 72.0 g (92% yield) of the mesylate which was used immediately for the further reaction. A solution of the mesylate (72.0 g, 334 mmol) and benzylamine (179.2 g, 1.6 mol) in DMSO (300 ml) was stirred at RT overnight. The reaction mixture was poured into 2 l of water and extracted with ethyl acetate (three times). The extracts were dried with MgSO4, thus yielding 75 g of a red oil after evaporation of benzylamine. The oil was used directly for the next reaction without further purification.

The synthetic route of 60753-14-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fisons Corporation; US4889941; (1989); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 134363-45-4, 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. 134363-45-4, name is 2-(Pyridin-3-yl)benzoic acid, molecular formula is C12H9NO2, 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.

A 250 ml_, round-bottomed flask under a positive pressure of nitrogen was equipped with a magnetic stirrer and charged with anhydrous DMF (70 ml_) followed by 2-[4-(4-amino-2-fluoro-phenyl)-piperazin-1 -yl]-N,N-diethyl-2- phenyl-acetamide (3.5 g, 9.1 mmol), 2-pyhdin-3-yl-benzoic acid (1.9 g, 9.5 mmol), HATU (3.8 g, 10.0 mmol) and DIPEA (1.3 g, 10.0 mmol). The resulting brown colored reaction mixture was stirred at ambient temperature for 16 h. The reaction mixture was then concentrated on the rotary evaporator to yield an oil. To this oil was added, dichloromethane (100 ml_) and 1 N NaOH (50 ml_). The biphasic solution was stirred for 0.5 h after which phases were separated. The aqueous layer was extracted with dichloromethane (2 X 25 ml_). The organic layers were pooled, dried over anhydrous sodium sulfate, filtered and concentrated to yield a viscous brown oil. The oil was taken in ethanol (100 ml_) and heated to -6O0C in a water bath for 1 h. The resulting mixture was diluted with MTBE (added with magnetic stirring in 25 ml_ portions, total 125 ml_). The resulting suspension was stirred at O0C (ice/water bath) for 2 h. The product was collected by filtration through a medium porosity glass frit, washed with a mixture of EtOH/MTBE (1 :1.25, 22.5 ml_ X 2) and the filter- cake dried thoroughly under house vacuum to yield the title compound as an off-white solid.MS (ESI): mass calcd. for C34H36FN5O2, 565.29; m/z found, 566.4 [M+H]+.1H-NMR(400 MHz, DMSO-d6) delta ppm: 10.65 (s, 1 H), 10.5 (bs, 1 H), 8.92 (s, 1 H), 8.82 (d, J = 5.5 Hz, 1 H), 8.39 (d, J = 7.6 Hz, 1 H), 7.96 (dd, J = 7.8, 5.6 Hz, 1 H), 7.76 (d, J = 7.6 Hz, 1 H), 7.70-7.63 (m, 4H), 7.56-7.50 (m, 4H), 7.26 (dd, J = 8.7, 1.7 Hz, 1 H), 7.02 (t, J = 9.4 Hz, 1 H), 5.97 (s, 1 H), 3.63-3.61 (m, 1 H), 3.48-3.15 (m, 10H), 2.67-2.65 (m, 1 H), 1.10-1.01 (m, 3H), 0.82-0.80 (m, 3H).

According to the analysis of related databases, 134363-45-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2009/6185; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 75806-86-9, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 75806-86-9 as follows.

Example 89: 5-Chloro-2-(2-fluoro-6-methoxy-phenoxy)-pyridin-3-ylamine; To a stirred solution of 2-bromo-5-chloro-3-nitropyridine (2.37 g, 10 mmol) was dissolved in 40 mL DMF was added of 2-methoxyl-6-fluorophenol (1.7 g 11.9 mmol) was added into the solution followed by potassium carbonate (2.76, 20 mmol). The mixture was stirred at room temperature for 5 h, then poured into ice water (200 mL). The precipitate was filtered and dried under high vacuum to provide 5-chloro-2-(2-fluoro-6-methoxy-phenoxy)-3-nitro-pyridine. [00491] AcOH (30 mL) and iron powder (5 g) were charged into a round bottom flask equipped with a magnetic stirring bar and warmed to 80 C. A solution of crude 5-chloro-2-(2-fluoro-6-methoxy-phenoxy)-3-nitro-pyridine in AcOH was added slowly into the mixture, keeping the temperature under 85 C. The reaction mixture was then cooled to room temperature, diluted with EtOAc, and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure and the residue was partitioned between NaHCO3 and EtOAc. The organic portion was separated and the aqueous portion was extracted with EtOAc. The combined extracts were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to provide 5-chloro-2-(2-fluoro-6-methoxy- phenoxy)-pyridin-3-ylamine (3.56 g) as a colorless powder.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,75806-86-9, its application will become more common.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2006/76644; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 178876-83-0 , The common heterocyclic compound, 178876-83-0, name is Methyl 6-amino-3-bromopicolinate, molecular formula is C7H7BrN2O2, 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 methyl 6-amino-5-bromopyridine-2-carboxylate (19. 8 g) (T. R. Kelly and F. Lang, J ; Org. Chem. 61, 1996,4623-4633) and 1-chloromethyl-4-fluoro-1, 4- diazoniabicyclo [2.2. 2] octane bis (tetrafluoroborate) (34.3 g) in acetonitrile (340 ml) under argon was heated to 40C for 1 hour, 60C for 1 hour and then 80C overnight. After partitioning between EtOAc and water (500ml each) the aqueous fraction was re- extracted with EtOAc (300 ml) and the combined organic solution dried with MgS04 and evaporated. Chromatography (20% then 30% EtOAc in hexane) separated various byproducts from the required ester (2.09 g). MS (+ve ion electrospray) m/z 249 and 251 (MH+, 100%)

The synthetic route of 178876-83-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM P.L.C.; WO2003/87098; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem