Day: September 13, 2021

Electric Literature of 17282-04-1, 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. 17282-04-1, name is 2-Chloro-3-fluoropyridine, molecular formula is C5H3ClFN, 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.

To a flask was charged with 2-chloro-3-fluoropyridine (1.163 g, 8.84 mmol) and THF (15 mL). The mixture was cooled to -78 C and then a solution of n-butyl lithium BuLi (2.83 ml, 7.07 mmol) in tolune solution was added dropwise. The mixture was aged at -78 C for 30 min, and a solution of (6R,8aS)-N-methoxy-N-methyl-3- oxooctahydroindolizine-6-carboxamide (1.0 g, 4.42 mmol) in THF ( 2.5 mL) was added dropwise by syringe. The resulting reaction mixture was stirred at -78 C for 2 hrs. The mixture was quenched with water at low temperature, extracted with EtOAc 3x, dried over MgS04, filtered and concentrated in vacuo to give crude. Crude was loaded and purified on 24 gr Redi Sep Rf filter column on CombiFlash with 10% MeOH/DCM 0- 3% to afford product (6R,8aS)-6-(2-chloro-3-fluoroisonicotinoyl)hexahydroindolizin- 3(2H)-one LC-MS (ES, m/z) Ci4H14ClF 202: 296; Found 297[M+H]+.

According to the analysis of related databases, 17282-04-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; KIM, Ronald, M.; KOZLOWSKI, Joseph; KRIKORIAN, Arto, D.; ANAND, Rajan; WO2015/95099; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 77992-44-0, 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 77992-44-0 as follows.

A mixture of [5-BROMO-PYRIDINE-2-YL-HYDRAZINE] (4.34 g, 23.1 [MMOL)] and isobutyryl chloride (21.8 mL, 0.208 mol) is [REFLUXED] gently for 3 hours. The mixture is cooled to room temperature. Hexane (22.0 mL) is added and the slurry is stirred at room temperature for 15 minutes and filtered. The cake is washed with hexane (3x) and dried in a vacuum-oven (30- [35C)] for 48 hours. The product (5.90 [G,] yield 92.3%) is obtained as an off-white powder. A biphasic mixture of the product (5.87 [G,] 21.2 [MMOL),] water (12.0 mL) and dichloromethane (18.0 mL) is cooled to 5-10 [C.] A [1N] aqueous solution of [NAOH] (21.5 mL) is added over a period of 10 minutes. The mixture is stirred in the bath for 15 minutes. The organic layer is isolated and the aqueous layer extracted with dichloromethane (2x). The combined organic extracts are washed with 1: 1 brine-water and dried [(MGS04). MOST] of the dichloromethane is removed in vacuo. Ethyl acetate (8.0 mL) is added. After removing about half of the solvents, hexane is added. The slurry is stirred in an ice-water bath for 2 hours and filtered. The cake is washed with 9: 1 hexane-Ethyl acetate (3x) and dried in a vacuum-oven [(30-35C)] for 18 hours. The title compound may be obtained as a sandy tan powder (4.72g, 92.5%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,77992-44-0, its application will become more common.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2004/20440; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 52605-98-8, 5-Bromo-2,3-dimethoxypyridine, 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 C7H8BrNO2, blongs to pyridine-derivatives compound. Computed Properties of C7H8BrNO2

Add 2,3-dimethoxy-5-bromopyridine (218mg, 1.0mmol) to 5mL N, N-dimethylformamide solution, add cuprous cyanide (179.2mg, 4.0mmol), protect with argon Then, the temperature was raised to 160 C, and the reaction was completed after 8 hours of reaction. Cooled to room temperature, diluted with water, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated to remove the solvent, and column chromatography (petroleum ether: ethyl acetate = 10: 1) to obtain the product 2,3- Dimethoxy-5-cyanopyridine (i.e. compound 16, 164.2 mg, 1.0 mmol), white solid, yield 50%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,52605-98-8, 5-Bromo-2,3-dimethoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Zhiyuan Pharmaceutical (Qingyuan) Co., Ltd.; Wu Deyan; Xie Ying; Zhou Huifang; (24 pag.)CN110498784; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 6000-50-6, 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. 6000-50-6, name is 2,3-Dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride. A new synthetic method of this compound is introduced below.

To a solution Intermediate 106 (500 mg, 1.34 minol) in THE (15 mL) was added at r.t. 4- nitrophenylchloroformate (270 mg, 1.34 minol) and the mixture stirred for 14 h at that temperature. After concentrating the mixture under reduced pressure the residue was taken upin dichloromethane (40 mL) and N,N-diisopropylethyl amine (0.78 mL, 4.4 minol) and 2,3- dihydro-1 H-pyrrolo[3,4-c]pyridine dihydrochloride (274 mg, 1 .42 minol) were added. The reaction mixture was heated to 6000 for 4h and then poured on water. After basification of the mixture with I N aqueous sodium hydroxide solution the mixture was extracted with dichloromethane (2x). The combined organic extracts were washed with brine and filtered through a phaseseparator filter. The residue on the filter was dried at 50°C under vacuum to give the titlecompound (446 mg, 1.03 minol, 72percent).1H-NMR (400 MHz, DMSO-d6): 6 [ppm] = 8.77 (s, IH), 8.71 (s, IH), 8.65 (d, IH), 7.76-7.64 (m,5H), 4.95-4.86 (m, 4H), 3.80 (br t, 2H), 3.60 (t, 2H), 2.84 (s, 2H), 1.09 (s, 6H).LC-MS (Method 6): Rt = 0.79 min; MS (ESIpos): mz = 408 [M÷H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6000-50-6, 2,3-Dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; GIESE, Anja; QUANZ-SCHOEFFEL, Maria; MUeLLER, Thomas; GUeNTHER, Judith; BOeHNKE, Niels; GRIEBENOW, Nils; BARAK, Naomi; BOeMER, Ulf; NEUHAUS, Roland; OSMERS, Maren; KOPITZ, Charlotte Christine; KAULFUSS, Stefan; REHWINKEL, Hartmut; WEISKE, Joerg; BADER, Benjamin; CHRISTIAN, Sven; HILLIG, Roman; (426 pag.)WO2018/86703; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6980-08-1, Adding some certain compound to certain chemical reactions, such as: 6980-08-1, name is 4-Chloro-3-nitropyridin-2-amine,molecular formula is C5H4ClN3O2, 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 6980-08-1.

To 400 mg (2.32 mmol) of 5-N-BOC-amino-8-hydroxy-quinoline dissolved in 30 mL DMF (dry), were added under stirring and argon atmosphere, 360 mg (3.20 mmol) tert-BuOK. After 30 minutes, 400 mg (2.32 mmol) 2-amino-3-nitro-4-chloropyridine were added at once and the reaction mixture heated at 850C (bath) for 5 hours. After cooling, 200 mL AcOEt were added and the solution extracted with 2 x 200 mL brine. The solution was dried (MgSO4) and evaporated under vacuum. The residue was purified on an lsolute column (Flash Si II; 50 g, 170 mL) eluted with AcOEt. The title compound was obtained as a yellow solid: 0.534 g. Yield: 58%. 1H NMR (500 MHz, DMSO-d6) delta: 1.51 (s, 9H, C(CH3J3), 5.65 (d, 1 H, HPyr, J=5.6 Hz), 7.14 (S, 2H1 NH2), 7.58-7.61 (m, 1 H1 HArom), 7.64 (d, 1 H, HArom, J= 8.3 Hz), 7.74 (d, 1 H, HArom, J= 8.3 Hz), 7.82 (d, 1 H, HPyr), 8.53-8.55 (m, 1H, Harom), 8.84-8.86 (m, 1H, Harom), 9.51 (S, 1 H, NH); LC-MS, tR = 6.51 min, m/z: 397.1 (M)+, calcd for C19H19N5O5.

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. 6980-08-1, 4-Chloro-3-nitropyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL (THE); WO2009/130487; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 116986-08-4, 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.116986-08-4, name is Methyl 2-(bromomethyl)nicotinate, molecular formula is C8H8BrNO2, molecular weight is 230.0586, as common compound, the synthetic route is as follows.

A mixture of 2,6-dihydroxybenzaldehyde (leq) and methyl 2-(bromomethyl)nicotinate (leq) was dissolved in anhydrous N,N-Dimethylformamide (DMF). Anhydrous potassium carbonate (K2CO3) (l.2eq) was added to this mixture and the reaction was stirred at room temperature for 4 hours. The solvent was then evaporated and the reaction mixture was extracted with ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered and the solvent evaporated. The crude product was purified using S1O2 column chromatography and eluted with the solvent system EtOAc: hexanes = 5:2 to obtain pure product as pale yellow powder with a yield of 58%. IR (Diamond, cm-1): 2956, 1713, 1618, 1637, 1571, 1459, 1435, 1396, 1370, 1287, 1238, 1 170, 1 141 ; 1H-NMR (400 MHz, DMSO-dfi): d 1 1.67 (s, 1H), 10.19 (s, 1 H), 8.75 (dd, .7= 4.8, 1.68 Hz, 1H), 8.25 (dd, J= 7.84, 1.68 Hz, 1 H), 7.55 (m, 2H), 6.66 (d, J = 8.2 Hz, 1 H), 6.53 (d, J = 8.4 Hz, 1H), 5.58 (s, 2H), 3.79(s, 3H); 13C-NMR (100 MHz, DMSO-d6): d 193.68, 166.15, 162.26, 161.44, 155.02, 151.73, 138.75, 138.31 , 126.02, 123.60, 1 10.66, 109.49, 103.51, 70.59, 52.50. MS (ESI) m/z found 288.09 (M+H)+, 310.07 (M+Na)+, Calculated 301.2940 [M]+. The purity of the compound was checked by HPLC and was found to be 100% pure.

The chemical industry reduces the impact on the environment during synthesis 116986-08-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; VIRGINIA COMMONWEALTH UNIVERSITY; THE CHILDREN’S HOSPITAL OF PHILADELPHIA; SAFO, Martin, K.; ZHANG, Yan; PARAGE, Piyusha, Pradeep; XU, Guoyan; GHATGE, Mohini; VENITZ, Jurgen; ABDULMALIK, Osheiza; (78 pag.)WO2019/182938; (2019); 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.88511-27-7, name is 4-Amino-3-iodopyridine, molecular formula is C5H5IN2, molecular weight is 220.0111, as common compound, the synthetic route is as follows.COA of Formula: C5H5IN2

General procedure: Procedure A : Suzuki coupling To a solution of iodopyridine (1 eq) in dioxane (5 mL/mmol), the boronic acid (1.5 eq), and 1 M Na2C03 aqueous solution (3 eq) were added and the reaction mixture was degassed with argon for 20 min. Then Bis(triphenylphosphine)palladium(ll) dichloride (0.2 eq) was added and the reaction mixture was heated at 100C for 16h. After completion of reaction, the reaction mixture was filtered through a celite pad and the filtrate was concentrated under reduced pressure to afford a residue that was dissolved in water and extracted with ethyl acetate. The organic layer was separated, dried over sodium sulphate and concentrated under reduced pressure to afford the crude product, which was further purified by silica gel (100:200 mesh) column chromatography to afford the Suzuki coupling product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,88511-27-7, 4-Amino-3-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; UCB BIOPHARMA SPRL; MERCIER, Joel; PROVINS, Laurent; VERMEIREN, Celine; SABNIS, Yogesh Anil; (106 pag.)WO2016/124508; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 77992-44-0, 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 77992-44-0 as follows.

INTERMEDIATE 1N-(5-Bromopyridin-2-yl)-2-[2-(difluoromethoxy)phenyllacetohydrazideTo a stirred solution of 2-(difluoromethoxy)phenylacetic acid (3.0 g, 14.85 mmol) in DCM (10 mL) at 0C was added triethylamine (4.4 g, 44.5 mmol), followed by EDCI (3.4 g, 21.90 mmol). The reaction mixture was stirred at 0C for 30 minutes. 5-Bromo-2- hydrazinopyridine (3.07 g, 16.4 mmol) was added and the reaction mixture was stirred at room temperature for 12 h, then diluted with DCM. The organic layer was washed with H20 and brine, then concentrated in vacuo. The crude material obtained was triturated with pentane and Et20 to give the title compound (3.90 g, 70%), which was used for the next reaction without any further purification. deltaEta (400 MHz, DMSO-d6) 10.09-9.90 (m, 1H), 8.67-8.44 (m, 1H), 8.12 (d, 1H, J2.4 Hz), 7.66 (dd, 1H, J 9.0, 2.4 Hz), 7.41 (dd, 1H, J7.6, 1.8 Hz), 7.37-7.26 (m, 1H), 7.26-7.09 (m, 3H), 6.58 (d, 1H, J 8.9 Hz), 3.58 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,77992-44-0, its application will become more common.

Reference:
Patent; UCB BIOPHARMA SPRL; BROOKINGS, Daniel Christopher; JACKSON, Victoria Elizabeth; WO2015/86496; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 109-09-1, 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.109-09-1, name is 2-Chloropyridine, molecular formula is C5H4ClN, molecular weight is 113.54, as common compound, the synthetic route is as follows.

General procedure: 20 mL scintillation vial was charged with a solution of MnCl2THF1.6 (3 mol%, 3 mg, 0.012mmol) in 3 mL THF in a glove box. The corresponding electrophile (0.41 mmol, 1 equiv.) andinternal standard, mesitylene (0.41 mmol, 1equiv.), were added. After five minutes of stirring atroom temperature, the Grignard solution (1.2- 2.6 equiv.) was added dropwise and the reactionwas stirred at room temperature. The reaction mixture was removed from the glovebox andquenched with a saturated K2CO3 solution (3 mL) and EtOAc (3 mL). The organic layer wasextracted with EtOAc (3 x 3mL), and dried over MgSO4. The solution was then filtered andconcentrated. The crude product was purified via a silica plug.

The chemical industry reduces the impact on the environment during synthesis 109-09-1, I believe this compound will play a more active role in future production and life.

Reference:
Article; Petel, Brittney E.; Purak, Merjema; Matson, Ellen M.; Synlett; vol. 29; 13; (2018); p. 1700 – 1706;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1000342-71-1, 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. 1000342-71-1, name is 6-Bromo-1H-pyrrolo[3,2-c]pyridine. A new synthetic method of this compound is introduced below.

General procedure: To a stirred solution of 5-bromo-1H-pyrrolo[2,3-c]pyridine (1.5 g, 7.61 mmol) in DMF (15 mL), KOH (1.27 g, 11.42 mmol) was added at RT. The resulting solution was stirred for 30 min. Then, fert-butyl 3- (bGammaomomethyl)piperidine-1-caoxylate (3.17 g, 22.84 mmol) was added at 0 C, and stirred at RT for 16h. The reaction mixture was diluted with water (70 mL) and extracted with EtOAc (2 x 70 mL), the combined organic layers were dried over anhydrous Na2SO4, and concentrated under reduced pressure. The crude compound was purified by flash column chromatography and eluted with 30% EtOAc/ pet ether to obtain the title compound (1.6 g, 54%) as an off white solid. LC-MS (method 1): Rt =2.47 min; m/z = 394.24 (M+H+)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1000342-71-1, 6-Bromo-1H-pyrrolo[3,2-c]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; ORYZON GENOMICS, S.A.; SALAS SOLANA, Jorge; CARCELLER GONZALEZ, Elena; ORTEGA MUNOZ, Alberto; (195 pag.)WO2018/149986; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem