Tag: M.W:200-300

Synthetic Route of 886365-47-5 , The common heterocyclic compound, 886365-47-5, name is 1-(5-Bromo-2-chloropyridin-3-yl)ethanone, molecular formula is C7H5BrClNO, 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.

Preparation of 5-bromo-3-methyl-1H-pyrazolo[3,4-b]pyridine (D-2-6).A mixture of compound D-2-5 (4 g, 16 mmol) and hydrazine (30 mL) in ethanol (300 mL) was stirred at room temperature overnight. TLC (petroleum ether/EtOAc 5:1 ) indicated complete consumption of starting material. The reaction mixture was concentrated in vacuo and the residue was purified via column chromatography (silica gel, petroleum ether/EtOAc 15:1 ) to yield crude compound D-2-6, which was further purified by preparative HPLC to yield pure compound D-2-6 (800 mg, yield: 20%) as a white solid.

The synthetic route of 886365-47-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; WO2009/16460; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 2897-43-0 ,Some common heterocyclic compound, 2897-43-0, molecular formula is C5H3Cl2N3O2, 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 a solution of 2,6-dichloro-3-nitro-pyridin-4-amine (2.6 g, 14.4 mmol) from Step A in MeOH (150 mL) was added Raney Nickel catalyst (2 g) and the reaction agitated under a hydrogen atmosphere in a Parr apparatus (35 p.s.i.) for 2 h . The reaction mixture was filtered through a pad of Celite and concentrated to yield the title compound. MS: m/z = 179 (M + 1).

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. 2897-43-0, 2,6-Dichloro-3-nitropyridin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; WO2007/61694; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 86847-84-9, name is N-(6-Chloropyridin-2-yl)pivalamide. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

B. 1 N-(6-chloro-3-iodopyridin-2-yl)pivalamide[0336] To a solution of N-(6-chloropyridin-2-yl)pivalamide (15.8 g, 74.2 mmol) in anhydrousTHF (150 mL) at -78 0C under a nitrogen atmosphere, is added 1.7 M -butyllithium in pentane (96 mL, 163 mmol, 2.2 eq.) dropwise (dropping funnel) over 0.5 h. The reaction mixture is then stirred at -78 0C for 3 h before iodine (22.6 g, 89 mmol, 1.2 eq.) in THF (60 mL) is slowly added in one portion. After 10 min., the cooling bath is removed and the reaction is allowed to warm to rt and stirred for 2 h. Hydrochloric acid (1 M, 75 mL) is then added to the reaction reaction mixture. The reaction mixture is concentrated in vacuo (rotary evaporator) to remove the THF, the resulting mixture is extracted with ethyl acetate (800 mL). The phases are separated and the organic layer is washed with aqueous 1 M Na2S2theta3 (100 mL), brine (300 mL x2), water (300 mL), dried over MgSO/t, and evaporated. The crude product is recrystalized from DCM/hexanes (1 :4) and the solid that forms collected by filtration to provide N-(6-chloro-3-iodopyridin-2-yl)pivalamide as a white crystalline solid (17.2 g). The filtrate is evaporated and the residue chromatographed on a silica gel column (hexanes/EtOAc, 9/1) to provide an additional product (2.5 g). Overall 19.7 g (78% yield) of N-(6-chloro-3-iodopyridin-2-yl)pivalamide is obtained. 1H NMR (300 MHz, DMSO-^6), delta 9.86 (s, IH), 8.30 (d, J = 8.4 Hz, IH), 7.20 (d, J = 8.4 Hz, IH), 1.23 (s, 9H). LCMS-ESI (m/z): calcd for C10H12ClIN2O 337.9; [M+H]+ found 339.0.

With the rapid development of chemical substances, we look forward to future research findings about 86847-84-9.

Reference:
Patent; GALAPAGOS N.V.; BURRITT, Andrew; WO2008/65198; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 89167-34-0, 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 89167-34-0 as follows.

A mixture of 4-chloro-3-iodopyridine (1.50 g, 6.30 mmol, prepared according to Tabanella, S. et al. Org. Biomol. Chem. 2003, 1, 4254-4261.), 2-fluoro-nitrophenol (Lancaster, 2.0 g, 12.7 mmol), DIPEA (5 mL), and NMP (10 mL) was heated at 150 C. After 12 h, more 2-fluoro-nitrophenol (0.50 g, 3.18 mmol) was added to the reaction mixture and heating was continued for 4 h. Most of the volatile components were removed under vacuum at 75 C., the residue treated with saturated aq. NaHCO3 solution (150 mL) and extracted with EtOAc (2×100 mL). The combined extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to give the crude product. Purification by flash chromatography on silica gel, using 0-100% CH2Cl2/hexanes then 2% MeOH/CH2Cl2 gave the title compound (1.0 g, 43%) as a yellow solid. 1H NMR (DMSO-d6) delta 8.96 (s, 1H), 8.47 (d, 2H, J=5.5 Hz), 8.44 (dd, 1H, J=2.7, 9.2 Hz), 7.49 (dd, 1H, J=8.8, 8.2 Hz), 7.07 (d, 1H, J=5.5 Hz); MS (ESI+): m/z 361.05 (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,89167-34-0, its application will become more common.

Reference:
Patent; Borzilleri, Robert M.; Cornelius, Lyndon A.M.; Schmidt, Robert J.; Schroeder, Gretchen M.; Kim, Kyoung S.; US2005/245530; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 867034-10-4 ,Some common heterocyclic compound, 867034-10-4, molecular formula is C10H9ClN2O2, 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 a heterogeneous solution of potassium ethoxide (6.56 g, 77.9 mmol) in diethyl ether (55 mL), was slowly added diethyl oxalate (10.6 mL, 77.9 mmol). A slight exotherm resulted. After stirring 5 min, a homogeneous yellow solution resulted, but after 10 min, a heterogeneous yellow slurry was observed. Addition of 2-chloro-4-methyl-3-nitropyridine (13.45 g, 77.9 mmol) as a solid, with a diethyl ether rinse (23 mL), resulted in a dark violet solution with a dark precipitate. The mixture was stirred at room temperature overnight (21 h). The solid precipitate was filtered, rinsed thoroughly with diethyl ether, and air-dried to give potassium (lZ)-1-(2-chloro-3- nitropyri din-4-yl)-3-ethoxy-3-oxoprop-1-en-2-olate (19.8 g, 63.6 mmol, yield 81%) as an orange solid. The crude product was used directly without further purification or identification.Potassium (lZ)-l-(2-chloro-3-nitropyridin-4-yl)-3-ethoxy- 3-oxoprop-1-en-2-olate (19.8 g, 63.6 mmol) was dissolved in acetic acid (908 mL) and the solution was treated with iron powder (14.6 g, 280.9 mmol). The reaction mixture was warmed to 60C and stirred overnight (18.5 h). TLC analysis indicated consumption of the starting material, therefore the reaction mixture was filtered through diatomaceous earth to remove the catalyst. The filtrate was concentrated to dryness. The residue was treated with methylene chloride (ca. 400 mL) and filtered through a plug of silica. Eluting with methylene chloride removed insolubles, and further elution with methylene chloride/ethyl acetate (50: 50) provided ethyl 7- chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (10.3 g, 45.8 mmol, yield 72%) as a yellow solid after concentration: Rf 0.80 (silica gel, 50:50 hexanes/ethyl acetate) ; mp 152-157C; (at)H NMR (300 MHz, CD30D) 81.43 (3H, t, J = 7.0 Hz), 4.44 (2H, q, J = 7.1 Hz), 7.27 (lH, s), 7.65 (1H, d, J = 5.7 Hz), 7.95 (1H, d, J = 5.4 Hz); ESI MS m/z 224 [C10H9ClN2O2 + H] +; HPLC (Method A) >99% (AUC) , tR = 16. 6 min.Ethyl 7-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (0.64 g, 2.85 mmol) was dissolved in tetrahydrofuran (5.7 mL) and methanol (6.8 mL). To the mixture was added 3 N KOH (2.85 mL). After stirring overnight (15.5 h) at room temperature, the reaction mixture was concentrated to dryness. The residue was dissolved in water. This aqueous solution was made acidic (pH 3 using 6 N HCl. The precipitate was collected by filtration. The precipitate was dissolved in methanol and concentrated to dryness to afford 7-chloro-lH-pyrrolo[2,3- c] pyridine-2-carboxylic acid (0.53 g, 2.7 mmol, 94%) as a yellow powder: mp 210-214C; ¹H NMR (300 MHz, CD30D) 87.25 (lH, s), 7.65 (lH, d, J = 5.4 Hz), 7.94 (lH, d, J = 5.4 Hz) ; ESI MS m/z 195 [C8H5ClN2O2 – H]-; HPLC (Method A) >99% (AUC) , tR = 12.2 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,867034-10-4, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2005/97129; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 114042-02-3, 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. 114042-02-3, name is 5-Bromo-3-methyl-2-nitropyridine, molecular formula is C6H5BrN2O2, 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.

(1) Add DMA and DMF to the reaction kettle,The molar ratio of DMA to DMF is 2:3.Stir and mix well,Thereafter, 2-nitro-3-methyl-5-bromopyridine is added thereto.Heat, keep the temperature at 160 C,Carry out a reflux reaction,After the reaction is completed,Distilling the solvent under reduced pressure,Add absolute ethanol,After mixing evenly, suction filtration, washing,Drying2-nitro-3-dimethylamine vinyl-5-bromopyridine

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 114042-02-3, 5-Bromo-3-methyl-2-nitropyridine.

Reference:
Patent; Jiaxing Xiuzhou Qu Hong Hezhen Middle School; Zhu Shengxiang; (6 pag.)CN109456323; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2897-43-0, 2,6-Dichloro-3-nitropyridin-4-amine, 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 C5H3Cl2N3O2, blongs to pyridine-derivatives compound. Computed Properties of C5H3Cl2N3O2

(6) 2,4,6-trichloro-3-nitropyridine 2,6-dichloro-3-nitropyridine-4-amine (2.27 g, 10.9 mmol) was added to 48 mL concentrated hydrochloric acid, and cooled to 0-5 C. To the solution was added sodium nitrite (2.26 g, 32.7 mmol) in batches. After the addition of sodium nitrite, the reaction solution was stirred for 1 h at 0-5 C., and then stirred for 2 h at 25 C., adjusted to pH=7 with 40% sodium hydroxide solution, and extracted with ethyl ether. After the organic phase was dried (Na2SO4) and concentrated, it was subjected to column chromatography eluted with petroleum ether to afford 2 g white solid with a yield of 80.7%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2897-43-0, 2,6-Dichloro-3-nitropyridin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; US2012/289497; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 885168-04-7, 5-Bromo-3-chloropicolinaldehyde, 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, HPLC of Formula: C6H3BrClNO, blongs to pyridine-derivatives compound. HPLC of Formula: C6H3BrClNO

5-Bromo-3-chloropicolylaldehyde 2.06 gAnd 1.00 g of 1-butylamineIn 10 ml of toluene,While performing azeotropic dehydration using a Dean-Stark tube,It was heated to reflux for 2 hours.Then,The solvent was distilled off under reduced pressure,To the residue was added acetic acid 10 mlAnd 1.05 g of nitroethane were added,Followed by stirring at 100 C. for 40 minutes.After completion of the reaction,The reaction mixture was allowed to cool to room temperature, 30 ml of water was added, and the mixture was extracted with ethyl acetate (50 ml × 2).The organic layers were combined, dried over anhydrous sodium sulfate and then saturated brine, dried,The solvent was distilled off under reduced pressure,The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (3: 97)0.76 g of the objective compound was obtained as brown crystals.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,885168-04-7, 5-Bromo-3-chloropicolinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; nissan chemical industries, Ltd.; Takeshi, Mita; Yuki, Tajima; Yusuke, Nanya; Kosay, Iwasa; Makoto, Inada; Miho, Asahi; (124 pag.)JP2017/39722; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1235036-15-3, Adding some certain compound to certain chemical reactions, such as: 1235036-15-3, name is tert-Butyl 3-bromo-6-chloropicolinate,molecular formula is C10H11BrClNO2, 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 1235036-15-3.

To Example 1.1.10 (100 mg) and tert-butyl3-bromo-6-chloropicolinate (52.5 mg) in dioxane(2 mL) was added tris(dibenzylideneacetone)dipalladium(O) (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 mixturewas stirred at 95 oc for 4 hours, diluted with ethyl acetate and washed with water and brine. Theorganic 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 providethe title compound. MS (ESI) m/e 643.3 (M+Ht

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. 1235036-15-3, tert-Butyl 3-bromo-6-chloropicolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBVIE INC.; BOGHAERT, Erwin, R.; JUDD, Andrew, S.; PHILLIPS, Andrew, C.; SOUERS, Andrew, J.; BRUNCKO, Milan; (503 pag.)WO2017/214301; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1026796-81-5, 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.1026796-81-5, name is N-(4-Bromopyridin-2-yl)acetamide, molecular formula is C7H7BrN2O, molecular weight is 215.05, as common compound, the synthetic route is as follows.

Intermediate 80: N-(4-(2-(Hydroxymethyl)-5-methyl-4-oxo-4,5-dihydrofuro[3,2-c]pyridin-7-yl)pyridin-2-yl)acetamide. 4,4,5,5-Tetramethyl-1 ,3,2-dioxaborolane (1 1.13 mL, 77 mmol) was added to a mixture of 7-bromo-2- (hydroxymethyl)-5-methylfuro[3,2-c]pyridin-4(5/-/)-one (for a preparation see Intermediate 78, 3.3 g, 12.79 mmol) and triethylamine (10.71 mL, 77 mmol) in 1 ,4-dioxane (20 mL) and the mixture was stirred for 5 min under nitrogen. Pd(PPh3)4 (1.478 g, 1 .279 mmol) was added and the mixture heated to 100C for 18 h. The mixture was cooled in an ice bath, then isopropanol (20.00 mL) was added, initially very cautiously, followed by water (10 mL), potassium carbonate (5.30 g, 38.4 mmol), PEPPSI-SIPr (0.871 g, 1.279 mmol) and A/-(4-bromopyridin-2-yl)acetamide (for a preparation see Intermediate 79, 3.02 g, 14.07 mmol). The mixture was heated to 80C for 2 h under nitrogen, then allowed to stand over the weekend. The mixture was diluted with ether (100 mL) and stirred for 10 min, then filtered and the solid was washed with water (50 mL) and dried under vacuum for 10 min to give the crude product. The resulting solid was heated in methanol (50 mL) to reflux, then cooled in an ice bath and the solid product collected by filtration to give A/-(4-(2-(hydroxymethyl)-5-methyl-4- oxo-4,5-dihydrofuro[3,2-c]pyridin-7-yl)pyridin-2-yl)acetamide (2.76 g, 8.81 mmol, 68.9 % yield) as a colourless solid. 1H NMR (400MHz, DMSO-of6) delta-ppm 10.53 (1 H, s), 8.50 (1 H, s), 8.38 (1 H, d), 8.13 (1 H, s), 7.48 (1 H, m), 6.85 (1 H, s), 5.46 (1 H, m), 4.55 (2H, d), 3.61 (3H, s), 2.13 (3H, s). LCMS (2 min, Formic): Rt = 0.55 min, MH+ 314.

Statistics shows that 1026796-81-5 is playing an increasingly important role. we look forward to future research findings about N-(4-Bromopyridin-2-yl)acetamide.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AMANS, Dominique; BAMBOROUGH, Paul; BARKER, Michael David; BIT, Rino Antonio; BROWN, John Alexander; CAMPBELL, Matthew; GARTON, Neil Stuart; LINDON, Matthew J; SHIPLEY, Tracy Jane; THEODOULOU, Natalie Hope; WELLAWAY, Christopher Roland; WESTAWAY, Susan Marie; WO2014/140077; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem