Category: pyridine-derivatives

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.1173897-86-3, name is 5-Bromo-6-methylpicolinonitrile, molecular formula is C7H5BrN2, molecular weight is 197.032, as common compound, the synthetic route is as follows.Application In Synthesis of 5-Bromo-6-methylpicolinonitrile

A suspension of 5-bromo-6-methylpyridine-2-carbonitrile (CAS 1173897-86-3, 0.195 g, 0.990 mmol), PdCl2(dppf) (0.072 g, 0.099 mmol), Z>w(pinocolato)diboron (0.352g, 1.386 mmol) and potassium acetate (0.194 g, 1.979 mmol) in dry DMSO (1.979 mL) was degassed (vacuum / nitrogen cycles) and heated in a sealed tube at 90 C for 4 h. The mixture was diluted with EtOAc, washed sequentially with water and brine, dried (phase separator) and concentrated in vacuo. The resulting residue was purified by flash chromatography (0-30% EtOAc in petrol on Si02) to afford the title compound. MS ES+: 245

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1173897-86-3, 5-Bromo-6-methylpicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; AHMED, Saleh; BARKER, Gregory; CANNING, Hannah; DAVENPORT, Richard; HARRISON, David; JENKINS, Kerry; LIVERMORE, David; WRIGHT, Susanne; KINSELLA, Natasha; (259 pag.)WO2016/148306; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 5470-22-4, 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.5470-22-4, name is 4-Chloropicolinic acid, molecular formula is C6H4ClNO2, molecular weight is 157.55, as common compound, the synthetic route is as follows.

A solution of 4-chloropicolinic acid (0.78 g, 5 mmol) in aqueous dimethylamine (40%, 10 ml) was stirred at 100 C for 5 h in a sealed tube. The resulting solution was concentrated in vacuo, then dissolved in EtOAc (50 ml) and washed with saturated aqueous NaHCO3 (50 ml) twice. The organic phase was dried over MgSO4 and evaporated in vacuo to afford compound 16 (0.79 g, 95%). 1H NMR (DMSO-d6, 400 MHz): delta 8.20 (d, J=7.48 Hz, 1H), 7.43 (d, J=2.98 Hz, 1H), 7.10 (dd, J1=3.01 Hz, J2=7.53 Hz, 1H), 3.27 (s, 6H). ESI-HRMS: m/z calcd for C8H10N2O2 [M+H]+ 189.0634 found 189.0638.

The chemical industry reduces the impact on the environment during synthesis 5470-22-4, I believe this compound will play a more active role in future production and life.

Reference:
Article; Lu, Chaocao; Htan, Bu; Fu, Shitao; Ma, Chunmiao; Gan, Quan; Tetrahedron; vol. 75; 30; (2019); p. 4010 – 4016;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 121643-46-7, 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 121643-46-7, name is 6-Chloro-2-methoxynicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 6-chloro-2-methoxynicotinonitrile (1.16 g, 6.88 mmol), 4-bromo-3-(1,3-dioxolan-2-yl)-2-fluorophenol (1.81 g, 6.88 mmol), potassium carbonate (1.14 g, 8.26 mmol), and N,N-dimethylformamide (35 mL) was stirred at 80 C. overnight. Water was added and the solution was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column using Combiflash to give 6-(4-bromo-3-(1,3-dioxolan-2-yl)-2-fluorophenoxy)-2-methoxynicotinonitrile (2.31 g, 85% yield).

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 121643-46-7, 6-Chloro-2-methoxynicotinonitrile.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; AKAMA, Tsutomu; US2015/291629; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 180995-12-4, 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.180995-12-4, name is 2,4-Dichloronicotinonitrile, molecular formula is C6H2Cl2N2, molecular weight is 173, as common compound, the synthetic route is as follows.

To a mixture of 5-amino-1-methyl-1 H-benzo[d]imidazol-2(3/-/)-one (750 mg, 4.6 mmol) and 2,4-dichloropyridine-3-carbonitrile (760 mg, 4.4 mmol) under argon was added DMA (10 mL) followed by DIPEA (0.90 mL, 5.19 mmol) . The reaction mixture was heated at 120C under microwave irradiation for 45 min then allowed to cool to rt and added dropwise to a stirring mixture of methanol:water (1 : 1 ; 120 mL). The resulting precipitate was filtered, washed with water (2 x 25 mL) and diethyl ether (2 x 30 mL) affording 2-chloro-4-[(1-methyl- 2-oxo-3/-/-benzimidazol-5-yl)amino]pyridine-3-carbonitrile (1297 mg, 99%, 4.3 mmol) as a beige solid. 1 H NMR (500 MHz, DMSO-cfe) delta 10.95 (br s, 1 H), 9.39 (br s, 1 H), 7.99 (d, J = 6.2 Hz, 1 H), 7.13 (d, J = 8.3 Hz, 1 H), 6.95 (dd, J = 8.3, 1.9 Hz, 1 H), 6.90 (d, J = 1.9 Hz, 1 H), 6.65 (d, J = 6.2 Hz, 1 H).

The chemical industry reduces the impact on the environment during synthesis 180995-12-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BELLENIE, Benjamin Richard; CARTER, Michael Keith; CHEUNG, Kwai Ming Jack; DAVIS, Owen Alexander; HOELDER, Swen; LLOYD, Matthew Garth; VARELA RODRIGUEZ, Ana; (381 pag.)WO2018/215801; (2018); 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.675198-19-3, name is (4-(3-Methoxypropoxy)-3-methylpyridin-2-yl)methanol hydrochloride, molecular formula is C11H18ClNO3, molecular weight is 247.72, as common compound, the synthetic route is as follows.HPLC of Formula: C11H18ClNO3

Example 1 : Preparation of 2-(chloromethyl)-4-(3-methoxypropoxy)-3-methyl pyridine (Formula V) Dichloromethane (300 mL) was added to [4-(3-methoxypropoxy)-3-methylpyridin-2- yl]methanol (Formula IV) hydrochloride (100 g) and the reaction mixture was cooled to -10C to -5C. Thionyl chloride (57.7 g) was added to the reaction mixture at -10C to -5C for 30 minutes to 60 minutes. The reaction mixture was stirred at -10C to -5C for 30 minutes to 60 minutes. The pH was adjusted to 7.0 to 7.5 with the aqueous sodium carbonate solution (prepared by dissolving 120 g of sodium carbonate in 500 mL of de-ionized water at 20C to 25C) at -10C to -5C. The temperature of the reaction mixture was raised to 0C to 5C. The mixture was allowed to settle for 10 minutes to 20 minutes and the layers obtained were separated. The organic layer was concentrated at 15C to 30C at 50 mm to 100 mm Hg of pressure. The residue obtained was dissolved in denatured spirit (100 mL). The mixture was concentrated at 15C to 30C at 20 mm to 30 mm Hg of pressure. The residue obtained was used in the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,675198-19-3, (4-(3-Methoxypropoxy)-3-methylpyridin-2-yl)methanol hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; KAPOOR, Ashwini, Kumar; CHATTERJEE, Pranab; NATH, Asok; PRASAD, Mohan; WO2014/91450; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 866546-07-8, 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 866546-07-8 as follows.

[94] Step 5. N-(3 -((5-Chloro- 1 Eta-rhonuetachi)1omicronGamma2.3 -blpyridin-3 -yl)(hvdroxy)-methyl)-2.4- difluorophenyl)- 1.1.2.2.3.3.3 -d7-propane- 1 -sulfonamide (24):; To a solution offormylsulfonamide 23 (50.0 mg, 0.185 mmol) in MeOH/Water 1 : 1 (1 mL) was added 5- chloroazaindole 6a(i) (30.0 mg, 0.196 mmol, Adesis, Inc.) followed by K2CO3 (171 mg, 1.24 mmol). The resulting solution stirred at room temperature for 3 days then was neutralized to pH 7 with 4N HC1 and extracted with EtO Ac (3 x 50 mL). The organic layers were combined, washed with water, dried (Na2S04), filtered and concentrated under reduced pressure to afford azaindole 24 (60 mg, 77%) as a tan solid which was used without further purification. MS (ESI) 421.0 [(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,866546-07-8, its application will become more common.

Reference:
Patent; CONCERT PHARMACEUTICALS INC.; TUNG, Roger; MASSE, Craig E.; SILVERMAN, I. Robert; WO2011/60216; (2011); A1;,
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. 74115-13-2, name is 5-Bromo-3-pyridinol, molecular formula is C5H4BrNO, 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. HPLC of Formula: C5H4BrNO

12a. 5-((2S)-Azetidinylmethyloxy)-3-bromopyridine dibenzoate Triphenylphosphine (4.01 g, 15.3 mmol) and DEAD (2.43 mL, 15.3 mnol) were dissolved in 30 mL of THF at 0 C., and the mixture was stirred for 10 minutes. Samples of 1-t-butyloxycarbonyl-2-(S)-azetidinemethanol (2.86 g, 15.3 mmol, Step 7c above) and 3-bromo-5-hydroxypyridine.(1.51 g, 10.2 mmol, Step 10c above) were added, and the mixture was stirred for 40 hours at room temperature. The volatile components were removed under vacuum, and the residue was triturated with hexane. The separated hexane fraction was concentrated, and the residue was chromatographed (silica gel; hexane/ether, 10:1 to 10:2) to afford 5-bromo-3-((1-t-butyloxycarbonyl-(2S)-azetidinyl)methoxy)pyridine as a colorless oil (1.669 g): 1 H NMR (CDCl3, 300 MHz) delta 1.42 (s, 9H), 2.31 (m, 2H), 3.89 (m, 2H), 4.12 (m, 1 H), 4.322 (m, 1 H), 4.52 (m, 1 H), 7.43 (m, 1 H), 8.29 (m, 2H); MS (CI/NH3) m/z 344 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 74115-13-2.

Reference:
Patent; Abbott Laboratories; US6133253; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 133362-99-9, 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. 133362-99-9, name is 2-Pyridin-4-ylbenzoic 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.

EXAMPLE 115 2-(4-Pyridinyl)-N-(4-{[2-(2-pyridinyl)ethyl]amino}phenyl)-benzamide The title compound was obtained from tert-butyl 4-aminophenyl[2-(2-pyridinyl)ethyl]carbamate and 2-(4pyridinyl)benzoic acid in the same manner as in Example 101. 1H-NMR (DMSO-d6): delta2.96 (2H, t, J=7.3 Hz), 3.28-3.44 (2H, m), 5.55 (1H, t, J=5.7 Hz), 6.52 (2H, d, J=8.8 Hz), 7.18-7.38 (4H, m), 7.46 (2H, dd, J=1.4 Hz, 10.2 Hz), 7.49-7.68 (4H, m), 7.70 (1H, dt, J=1.8 Hz, 7.6 Hz), 8.51 (1H, d, J=4.1), 8.57 (2H, d, J=6.0 Hz), 9.94 (1H, s) (+)APCI-MS (m/z): 395 (M+H)+

According to the analysis of related databases, 133362-99-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takasugi, Hisashi; Terasawa, Takeshi; Inoue, Yoshikazu; Nakamura, Hideko; Nagayoshi, Akira; Ohtake, Hiroaki; Furukawa, Yoshiro; Mikami, Masafumi; Hinoue, Kazumasa; Ohtsubo, Makoto; US2004/58903; (2004); 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: 117519-09-2, 3-Amino-2-chloro-6-(trifluoromethyl)pyridine, 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: C6H4ClF3N2, blongs to pyridine-derivatives compound. HPLC of Formula: C6H4ClF3N2

To a solution of 2-chloro-6-(trifluoromethyl)pyridin-3-amine (8) (5.0 g, 25 mmol) in acetonitrile (60 mL) was added NBS (5.0 g, 28 mmol). The mixture was stirred at reflux for 3 hours, concentrated and purified by silica gel chromatography and eluted with petroleum ether which gave 4-bromo-2-chloro-6-(trifluoromethyl)pyridin-3-amine (9) as a red semi-solid (6.0 g, 86% yield). 1H NMR (400 MHz, CDCl3) delta 7.68 (s, 1H), 4.93 (s, 2H). LCMS (ESI) m/z 275, 277 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,117519-09-2, 3-Amino-2-chloro-6-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; PLANKEN, Simon; CHENG, Hengmiao; COLLINS, Michael Raymond; SPANGLER, Jillian Elyse; BROOUN, Alexei; MADERNA, Andreas; PALMER, Cynthia; LINTON, Maria Angelica; NAGATA, Asako; CHEN, Ping; US2019/233440; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem