Category: pyridine-derivatives

Synthetic Route of 866755-20-6, 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. 866755-20-6, name is 2,6-Dichloro-3-bromopyridine, molecular formula is C5H2BrCl2N, 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 mixture of 3-bromo-2,6-dichloropyridine (4.5 g, 20 mmol ) and tert-butyl ((l S,3S)-3-hydroxycyclobutyl)carbamate (see PREPARATION 4A; 3.65 g, 20 mmol) in acetonitrile (50 mL) was added CS2CO (13.2 g, 40 mmol), and then the mixture was stirred at RT overnight. The reaction mixture was filtered and concentrated under vacuum to give tert- butyl ((l S,3S)-3-((3-bromo-6-chloropyridin-2-yl)oxy)cyclobutyl)carbamate (4.2 g, 11.2 mmol, 56%). ESI-MS (M+1): 377 calc. for Ci4Hi8BrClN203 376.

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 866755-20-6, 2,6-Dichloro-3-bromopyridine.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer; FROHN, Michael; HARRINGTON, Paul; PICKRELL, Alexander; RZASA, Robert; SHAM, Kelvin; HU, Essa; WO2011/143366; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 65156-94-7, name is 5-Chloro-1H-pyrrolo[3,2-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C7H5ClN2

A mixture of 5-chloro-lH-pyrrolo[3,2-b]pyridine (450 mg, 2.95 mmol, 1 equiv), (1344) CS2CO3 (960.9 mg, 2.95 mmol, 1 equiv) and iodomethane (418.6 mg, 2.95 mmol, 1.000 equiv) in DMF (11.2 mL), was stirred for 4 h at 60 C. The reaction was quenched by the addition of 30 mL of water, extracted with 10 ml of ethyl acetate and the combined organic layers concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1 : 10) as eluent to afford the desired final product as a yellow oil in 81% yield.

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, 65156-94-7, 5-Chloro-1H-pyrrolo[3,2-b]pyridine.

Reference:
Patent; IDEAYA BIOSCIENCES, INC.; ALAM, Muzaffar; ASWAD, Fred; BECK, Hilary Plake; DILLON, Michael Patrick; GONZALEZ-LOPEZ, Marcos; HATA, Yujiro; RICO, Alice Chen; SUTTON, JR., James Clifford; (342 pag.)WO2020/18848; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6311-35-9, 6-Bromonicotinic acid, 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, COA of Formula: C6H4BrNO2, blongs to pyridine-derivatives compound. COA of Formula: C6H4BrNO2

Step 1: 6-Chloronicotinamide To a solution of 6-bromopyridine-3-carboxylic acid (50 g, 247 mmol) in DCM (1 L) and DMF (3 mL) at room temperature was dropwise added oxalyl dichloride (80 mL). The mixture was stirred for 30 min at room temperature. The solvent was removed under reduced pressure and ammonia (1 L, 25-28% aqueous solution) was added dropwise. The resulting mixture was stirred for a further 1 h at room temperature. The solvent was evaporated in vacuo to yield 43 g of the crude product, which was used directly in the next step without further purification. LCMS (ESI): [M+H]+=157/159.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6311-35-9, 6-Bromonicotinic acid, and friends who are interested can also refer to it.

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

Reference of 6298-19-7, Adding some certain compound to certain chemical reactions, such as: 6298-19-7, name is 2-Chloropyridin-3-amine,molecular formula is C5H5ClN2, 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 6298-19-7.

12.8 g of 2-chloro-3-aminopyridine was suspended in 120 mL of 60% aqueous hexafluorophosphoric acid, and 9.0 g sodium nitrite was added little by little thereto at 0C to precipitate crystals. The crystals were collected by filtration and washed with diethyl ether to give 15.75 g diazonium salt. Subsequently, the diazonium salt was suspended in 100 mL xylene and heated at 85C for 3 hours, 28 mL triethylamine was added thereto, and the reaction mixture was diluted with an aqueous saturated sodium bicarbonatesolution and then extracted with ethyl acetate. The extract was washed with brine, and the organic layer was dried over anhydrous sodium sulfate and then filtered through silica gel. The ethyl acetate was removed, and to the resulting xylene solution was added 6.0 mL 2-aminoethanol, and the mixture was heated at 130C for 10 hours. Then, the same procedure as in Production Example 231 was carried out, whereby 385 mg of the title compound (yellowoil) was obtained as a mixture.1H-NMR (CDCl3) delta: 3.60-3.68(m, 2H), 3.84(t, J=4.8Hz, 2H), 6.52-6.60(m, 1H), 7.12-7.20(m, 1H), 7.80-7.85(m, 1H)

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. 6298-19-7, 2-Chloropyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai Co., Ltd.; EP1382603; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 78686-79-0 ,Some common heterocyclic compound, 78686-79-0, molecular formula is C7H5BrClNO2, 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.

Compound WX069-1 (7.00 g, 27.95 nmol) wasdissolved in dimethyl sulfoxide solution (50.00 mE) at roomtemperature, followed by the addition of cesium fluoride(8.00 g, 52.67 mmol) at room temperature. The reactionmixture was heated to 550 C. and stirred for 14 hours. Afterthe reaction, the mixture was cooled to room temperature,quenched with saturated brine (10 mE), diluted with water(50 mE) and extracted with ethyl acetate (20 mLx3). Thecolunm c1omatography (eluent: petroleum ether/ethylorganic phases were separated, washed with water (50mEx2) and dried over anhydrous sodium sulfate, followedby filtration. The filtrate was concentrated under reducedpressure. The obtained residue was isolated by silica gelacetate1 00/1 – 100/15, volume ratio) to obtain the targetproduct WX069-2. ?H NMR (400 MHz, CDC13) oe: 8.64-8.31 (m, 2H), 3.98 (s, 3H).

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. 78686-79-0, Methyl 5-bromo-2-chloronicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SHIJIAZHUANG SAGACITY NEW DRUG DEVELOPMENT CO., LTD.; LUO, Yunfu; YANG, Chundao; LEI, Maoyi; LIU, LING; HU, Guoping; LI, Jian; CHEN, Shuhui; US2019/177318; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1539-42-0 , The common heterocyclic compound, 1539-42-0, name is Bis(pyridin-2-ylmethyl)amine, molecular formula is C12H13N3, 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.

Di-(2-picolyl)amine (5.0 mmol, 900 muL)was dissolved in THF (10 mL). K2CO3 (20 mmol, 2.76 g) wasadded followed by dropwise addition of propargyl bromide (80% in toluene, 5.0mmol, 557 muL). The reaction mixture was stirred for 16 hrs before diluted withDCM. The diluted reaction mixture was filtrated through a pad of K2CO3under vacuum before concentrated. Compound 2was isolated in 96% yield from an alumina column elutedby EtOAc in DCM (0% – 40%). 1H-NMR(500 MHz, CDCl3, ppm) delta = 8.52(m, 2H), 7.62 (td, J = 2.0, 7.5 Hz, 2H), 7.47 (d, J= 8.0 Hz, 2H), 7.12 (td, J = 1.0, 5.0Hz, 2H), 3.88 (s, 4H), 3.37 (d, J =2.0 Hz, 2H), 2.27 (t, J = 2.5 Hz,1H); 13C-NMR (125 MHz, CDCl3,ppm) delta =153.6, 129.6, 83.6, 45.2, 34.6, 32.3, 26.5, 24.9.

The synthetic route of 1539-42-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yao, Zi-Jian; Hong, Shibin; Zhang, Wei; Liu, Mengyan; Deng, Wei; Tetrahedron Letters; vol. 57; 8; (2016); p. 910 – 913;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 73027-79-9, Adding some certain compound to certain chemical reactions, such as: 73027-79-9, name is 4,6-Dichloronicotinic acid,molecular formula is C6H3Cl2NO2, 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 73027-79-9.

To a solution of 4,6-dichloronicotinic acid (300 mg) in N,N-dimethylacetamide (4.0 mL) were added 2-(7-azabenzotriazol-1-yl)-1,1,3,3-hexafluorophosphate (HATU) (0.89 g), diisopropylethylamine (0.55 mL) and dimethylamine hydrochloride (190 mg), and the mixture was stirred overnight at room temperature. The reaction mixture was cooled to 0 C., saturated aqueous sodium hydrogencarbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (hexane/ethyl acetate) to give the title compound (240 mg). MS(ESI+): [M+H]+ 218.7.

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. 73027-79-9, 4,6-Dichloronicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; Saitoh, Morihisa; Yogo, Takatoshi; Kamei, Taku; Tokunaga, Norihito; Ohba, Yusuke; Yukawa, Takafumi; (191 pag.)US2016/159773; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 139585-70-9, 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 139585-70-9, name is 6-Bromonicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

Under an argon atmosphere, tert-butyl (2-{methyl[3-(2-piperazin-1-ylpyrimidin-5-yl)benzyl]amino}-2-oxoethyl)carbamate (200 mg) and 6-bromonicotinonitrile (124 mg) were dissolved in toluene (6 ml), and tris(dibenzylideneacetone) dipalladium (124 mg), 1,1′-binaphthalene-2,2′-diylbis(diphenylphosphine) (169 mg), and cesium carbonate (222 mg) were added thereto, followed by stirring at 100 C. for 6 hours. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (0% to 7% MeOH/CHCl3) to obtain tert-butyl {2-[(3-{2-[4-(5-cyanopyridin-2-yl)piperazin-1-yl]pyrimidin-5-yl}benzyl)(methyl)amino]-2-oxoethyl}carbamate (122 mg).

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 139585-70-9, 6-Bromonicotinonitrile.

Reference:
Patent; Astellas Pharma Inc.; US2012/184520; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 97483-77-7, 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 97483-77-7, name is 5-Bromopicolinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

Step 1 Preparation of (5-Bromo-pyridin-2-ylmethyl)-carbamic acid tert-butyl ester To a solution of 5-Bromo-pyridine-2-carbonitrile (1.0 g, 5.46 mmol) in methanol (10 mL) at 0 C. is added NiCl2.6H2O (0.12 g, 0.54 mmol), Di-tert-butyl dicarbonate (2.38 g, 0.010 mmol) and NaBH4 (0.413 g, 0.010 mmol) at 0 C. then stirred at room temperature for 14 hours. The reaction solvent is removed under reduced pressure and crude is diluted with water and ethyl acetate. The organic layer was separated, dried over sodium sulphate and concentrated in vacuum. The crude is purified by column chromatography eluting with 30% ethyl acetate in hexane to afford the title compound (650 mg). 1H-NMR (400 MHz, CDCl3) delta: 1.44 (s, 9H), 4.37 (d, J=5.44 Hz, 2H), 5.41 (bs, 1H), 7.18 (d, J=8.28 Hz, 1H), 7.75-7.78 (dd, J1=8.32 Hz, J2=2.28 Hz, 1H), 8.57 (d, J=2.08 Hz, 1H). LC-MS (m/z): [M+H]=289.0.

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 97483-77-7, 5-Bromopicolinonitrile.

Reference:
Patent; Curtis, Michael; Duclos, Brian A.; Ewin, Richard A.; Johnson, Paul D.; Johnson, Timothy Allen; Vairagoundar, Rajendran; Billen, Denis; Goodwin, Richard M.; Haber-Stuk, Andrea K.; Kyne, Graham M.; Sheehan, Susan M. K.; US2013/237502; (2013); A1;,
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 139585-70-9, name is 6-Bromonicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows. name: 6-Bromonicotinonitrile

lOld (59 mg, 0.19 mmol), 2-bromo-5-cyanopyridine (52 mg, 0.28 mmol), trans- dichlorobis(triphenylphosphine)palladium (II) (14 mg, 0.02 mmol), and copper(I) iodide (6 mg, 0.03 mmol) were mixed in a round bottom flask and placed under a nitrogen atmosphere. THF (1 mL) and triethylamine (0.053 mL, 0.380 mmol) were added, and the reaction mixture was stirred at 60 C for 1.5 hours. The reaction mixture was cooled to room temperature and diluted with EtOAc. The mixture was washed with sat’d aqueous NH4CI followed by brine, dried over MgSO/i, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0 to 50% EtOAc in heptane) gave 6-((3-((lS,5S,6S)-3-amino-l,5- bis(fluoromethyl)-2-thia-4-azabicyclo[4.1.0]hept-3-en-5-yl)-4- fluorophenyl)ethynyl)nicotinonitrile (101, 33 mg, 0.08 mmol, 42% yield) as an off-white solid. LC/MS (ESI+) m/z = 413.1 [M+H]+. NMR (400 MHz, DMSO-d6) delta ppm 9.05 (d, J = 1.37 Hz, 1H) 8.38 (dd, J = 8.22, 2.15 Hz, 1H) 7.96 (dd, J = 7.63, 2.15 Hz, lH) 7.85 (d, J = 8.22 Hz, 1H) 7.67 (ddd, J = 8.31, 4.50, 2.25 Hz, 1H) 7.35 (dd, J = 11.93, 8.41 Hz, 1H) 6.54 (s, 2H) 4.58 – 4.77 (m, 2H) 4.38 – 4.58 (m, 2H) 1.85 (t, J = 8.12 Hz, 1H) 1.19 (dd, J = 9.68, 5.38 Hz, 1H) 0.58 – 0.64 (m, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 139585-70-9.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; AMEGADZIE, Albert; BOURBEAU, Matthew P.; CHEN, Jian J.; FROHN, Michael J.; HARRINGTON, Paul E.; LOW, Jonathan D.; MA, Vu V.; NGUYEN, Thomas T.; PICKRELL, Alexander J.; REEVES, Corey; (122 pag.)WO2018/112086; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem