Category: 13534-97-9

Electric Literature of 13534-97-9, 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.13534-97-9, name is 6-Bromopyridin-3-amine, molecular formula is C5H5BrN2, molecular weight is 173.0106, as common compound, the synthetic route is as follows.

Example 1; 6-Bromo-3-pyridnoI.; 3-Amino-6-bromopyridinc (1.73 g, 10 mmol) was dissolved in HBF4 (5 mL, 50 % aq.) and water (5 mL) was added. To the resulting brownish solution, cooled to O0C in an ice-bath, NaNO2 (759 mg, 11 mmol) in water (5 mL) was added dropwisc. The resulting yellowish heterogenous reaction mixture was stirred for 1 h at this temperature. After addition of water (5 mL), the mixture was stirred in an oil -bath for 5 h at 1000C (gas evolution). The cooled reaction mixture was then neutralized by addition OfNaHCO3 (5 % aq.) and the product extracted with ethyl acetate (5 x 35 mL). After drying (NaiSO4) and evaporation in vacuo, the resulting brownish solid was purified by column chromatography (SiO2) using pentane/ethyl acetate (9:1) to give 1.04 g (60 %) of the title compound, mp 137-1380C (lit. 135.5-136.5 0C; den Hertog et al Rec. Tray. Chim. Pays-Bas 1959, 69, 1281).

The chemical industry reduces the impact on the environment during synthesis 13534-97-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; KAROLINSKA INSTITUTET INNOVATIONS AB; WO2009/144253; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13534-97-9, Adding some certain compound to certain chemical reactions, such as: 13534-97-9, name is 6-Bromopyridin-3-amine,molecular formula is C5H5BrN2, 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 13534-97-9.

Example 1; Preparation of intermediates N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(2-hydroxypropan-2-yl)benzamide (1D) and N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(trifluoromethyl)benzamide (1E); Step A: Commercially available 6-bromopyridin-3-amine (1A, 20 g, 1.0 equivalent) was added in portions to a solution of potassium thiocyanate (5.0 equivalents) in acetic acid (0.4 M) at -5° C. After addition, the mixture was cooled to -15° C., and a solution of Br2 (1.3 equivalent) in acetic acic (9.4 M) was added drop wise via an additional funnel. The mixture was then warmed to room temperature and stirred for 12 h. The resulting precipitate was filtered; 100 mL EtOAc and 200 mL H2O were added to the filtrate and then 200 mL of solvent was removed in vacuo. The residue was stirred in ice bath for 10 minutes, and then the resulting precipitate was collected by filtration and washed twice with cold 10percent MeOH in Et2O. The filtrate was concentrated and the product was crystallized in ice bath to obtain a second crop of product after washing twice with cold 10percent MeOH in Et2O. The product 1B (77percent) was obtained as a brown solid after drying under vacuum, and then used without further purification. 1H NMR (400 MHz, DMSO-d6) delta ppm 4.94 (br. s., 1H) 7.44 (d, J=8.34 Hz, 1H) 7.57 (d, J=8.34 Hz, 1H) 8.04 (br. s., 1H); ESI-MS: m/z 230.0 (M+H)+.

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. 13534-97-9, 6-Bromopyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/318425; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13534-97-9, 6-Bromopyridin-3-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, Application In Synthesis of 6-Bromopyridin-3-amine, blongs to pyridine-derivatives compound. Application In Synthesis of 6-Bromopyridin-3-amine

To a solution of 6-bromopyridin-3-amine (4.0 g, 23.25 mmol) in DCM (60 mL) was added pyridine (5.51 g, 69.75 mmol) and 3-chloropropanoyl chloride (3.515 g, 27.9 mmol) at 0°C and allowed to stir at RT for 12. The reaction mixture was diluted with DCM (200 mL) and washed with water (100 mL) and brine solution (100 mL). (0601) The separated organic layer was dried over anhydrous NBISOA, filtered and concentrated under reduced pressure to afford the title compound (4.5 g, 73percent) as a brown colour liquid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13534-97-9, 6-Bromopyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; ORYZON GENOMICS, S.A.; CARCELLER GONZALEZ, Elena; ORTEGA MUNOZ, Alberto; SALAS SOLANA, Jorge; (129 pag.)WO2018/219478; (2018); A1;,
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. 13534-97-9, name is 6-Bromopyridin-3-amine. A new synthetic method of this compound is introduced below., Quality Control of 6-Bromopyridin-3-amine

5′-((6-bromopyridin-3-yl)carbamoyl)-2′-methoxy-[1,1′-biphenyl]-3-yl acetate (21a): A solution of acid chloride 10b (300 mg, 1.16 mmol) in dichloromethane (1 ml) was added to a solution of 6-bromopyridin-3-amine (200 mg, 1.16 mmol) and pyridine (162 mg, 2.32 mmol) in dry dichloromethane (5 mL). The solution was then stirred at room temperature for 4 hours. After 4 hours, the reaction mixture was concentrated to dryness and the remaining residue was purified via column chromatography (SiO2, 10:1, CH2Cl2:methanol) to afford desired product as a light brown solid (416 mg, 87percent). 1H NMR (500 MHz, chloroform-d) delta 8.47 (d, J = 2.8 Hz, 1H), 8.21 (s, 1H, NH), 8.17 (dd, J = 8.7, 2.9 Hz, 1H), 7.88 (dd, J = 8.6, 2.4 Hz, 1H), 7.78 (d, J = 2.4 Hz, 1H), 7.44 (d, J = 8.6 Hz, 1H), 7.32 (t, J = 7.9 Hz, 1H), 7.09 ? 6.98 (m, 3H), 6.90 (dd, J = 8.2, 2.7 Hz, 1H), 3.88 (s, 3H), 3.83 (s, 3H). 13C NMR (126 MHz, CDCl3) delta 165.77, 159.94, 159.48, 141.64, 138.72, 136.00, 134.87, 130.96, 130.41, 129.84, 129.37, 128.84, 128.23, 126.05, 122.07, 115.57, 113.06, 111.32, 56.07, 55.52. HRMS (ESI+) m/z: [M + H+] calcd for C21H18BrN2O4 441.0450; found 441.0453.

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, 13534-97-9, 6-Bromopyridin-3-amine.

Reference:
Patent; THE UNIVERSITY OF KANSAS; BLAGG, Brian, S.J.; ZHAO, Huiping; WO2015/70091; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13534-97-9, 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 13534-97-9 as follows.

Step 1: 5-Bromothiazolo[5,4-b]pyridin-2-amine To a suspension of 6-bromopyridin-3-amine (20.0 g, 115 mmol) and potassium thiocyanate (56.0 g, 576 mmol) in acetic acid (250 mL) was added dropwise a solution of bromine (23.88 g, 149 mmol) in acetic acid (100 mL) at room temperature. The reaction mixture was stirred at room temperature for 15 h. The solids were filtered out, and then the resulting solution was extracted with ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate, filtered and the filtrate was evaporated in vacuo. The crude product was purified via flash chromatography on silica gel (solvent gradient: 0-10% methanol in DCM) to yield 18 g (68%) of the title compound. LCMS (ESI): [M+H]+=230/232.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13534-97-9, its application will become more common.

Reference:
Patent; Genentech, Inc.; Braun, Marie-Gabrielle; Garland, Keira; Hanan, Emily; Purkey, Hans; Staben, Steven T.; Heald, Robert Andrew; Knight, Jamie; Macleod, Calum; Lu, Aijun; Wu, Guosheng; Yeap, Siew Kuen; (183 pag.)US2018/65983; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13534-97-9, 6-Bromopyridin-3-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, SDS of cas: 13534-97-9, blongs to pyridine-derivatives compound. SDS of cas: 13534-97-9

To a solution of 6-bromopyridin-3-amine (500 mg, 2.89 mmol) in CH3CN:DMF (3:2 mL) was added CuI (219 mg, 1.15 mmol) and triethylamine (2 mL, 14.4 mmol) and the solution was purged with argon for 15 min. Ethynyltrimethylsilane (1.2 mL, 8.67 mmol) and tetrakis(triphenyl phosphine)Pd(0) (100 mg, 0.086 mmol) were added and the solution was purged for another 30 min. The reaction mixture was heated to 45C for 2.5 h. Then, the reaction mixture was diluted with ethyl acetate (100 mL) and washed with saturated NaHCO3 solution (50 mL). The aqueous layer was re-extracted with ethyl acetate (3 X 50 mL). The combined organic layer was washed with water (2 X 50 mL), followed by brine and dried over sodium sulphate and concentrated in vacuo to afford 6-((trimethylsilyl)ethynyl)pyridin-3-amine 5 (776mg, 70percent).1H NMR (400 MHz, CDCl3) delta 8.04 (s, 1H), 7.25 (d, J=7.8 Hz, 1H), 6.91(d, J=7.8 Hz, 1H), 3.85 (br s, 2H), 0.24 (s, 9H). ES-MS m/z 191.00 (M+H)+.

The synthetic route of 13534-97-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; LANSBURY, Peter, T.; GOOD, Andrew, C.; BOURQUE, Elyse Marie, Josee; (134 pag.)WO2016/73889; (2016); 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.13534-97-9, name is 6-Bromopyridin-3-amine, molecular formula is C5H5BrN2, molecular weight is 173.0106, as common compound, the synthetic route is as follows.COA of Formula: C5H5BrN2

To a solution of 3-amino-6-bromopyridine (1.1 g, 6.4 mmol) in THF (7 mL)-MeOH (7 mL) at RT was added phenylboronic acid (1.60 g, 12.8 mmol), PXPd (69 mg, 0.13 mmol), followed by K2CO3 (3.54 g, 25.6 mmol). The reaction mixture was stirred at 70° C. in a preheated oil bath for 16 h. After cooling to RT, the reaction mixture was poured into water (10 mL), and the resultant mixture was extracted with EtOAc (3.x.40 mL). The combined organic layers were washed with saturated NaCl, dried (Na2SO4), filtered and concentrated. The resulting residue was purified by silica gel (40 g) column chromatography eluting with a gradient of EtOAc (30-100percent) in hexane to give the title compound as an off-white solid (940 mg, 86percent). LC/MS (method A): retention time=1.28 min, (M+H)+=171.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13534-97-9, 6-Bromopyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; Sun, Chongqing; Ewing, William R.; Huang, Yanting; US2006/154955; (2006); 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.13534-97-9, name is 6-Bromopyridin-3-amine, molecular formula is C5H5BrN2, molecular weight is 173.0106, as common compound, the synthetic route is as follows.Quality Control of 6-Bromopyridin-3-amine

Intermediate 51; 6-(2,6-Difluorophenyl)pyridin-3-amineIn a three neck round bottle flask, to a mixture of 1 ,3-difluorobenzene (23.24 mmol, 2.29 ml) in THF (30 ml) at -780C under argon atmosphere, a solution of n-BuLi (10.2 ml) in THF (2.5M) was added. The mixture was stirred at -78°C for 30 minutes and then it was heated to -5O0C. A solution of ZnCI2 (51 ml) in THF (0.5M) was added drop wise and the mixture was stirred at this temperature for 20 minutes. A solution of 6-bromopyridin-3-amine (11.56 mmol, 2.0 g) in THF (20 ml) and Pd(PPh3)4 (1.16 mmol, 1.3 g) were added respectively and the crude mixture was heated at 4O0C overnight. The solvent was evaporated and the crude mixture was purified by reverse phase chromatography eluting with a water-MeOH/AcN system affording 0.72 g (yield 30percent) of the expected product, delta 1H NMR (200 MHz, CDCI3): 3.83 (s, 2H), 6.95-7.00 (m, 2H), 7.06-7.09 (d, 1 H), 7.23- 7.32 (m, 2H)1 8.24 (s, 1 H). ESI/MS (m/e, percent): 207 [(M+1)\ 100].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13534-97-9, 6-Bromopyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; LABORATORIOS ALMIRALL, S.A.; WO2009/21696; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem