Tag: M.W:100-200

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.5096-11-7, name is (S)-1-(3-Pyridyl)ethanol, molecular formula is C7H9NO, molecular weight is 123.15, as common compound, the synthetic route is as follows.Computed Properties of C7H9NO

EXAMPLE 6 (+)-(R)-1-(3-Pyridyl)ethyl 1-adamantanecarboxylate The method followed that described in Example 1, but using (+)-(R)-1-(3-pyridyl)ethanol [87% ee; prepared by asymmetric reduction of 3-acetylpyridine with (+)-B-chlorodiisopinocampheyl borane, J. Chandrasekharan, P. V. Ranachandran and H. C. Brown, J. Org. Chem., 50, 5446-5448 (1985)] (0.62 g, 5.0 mmol) in THF (20 ml), n-butyllithium (2.5 M; 2.0 ml, 5.0 mmol) in hexane, and 1-adamantanecarbonyl chloride (1.09 g, 5.5 mmol) in THF (5 ml). Chromatography, on elution with ether-petrol-triethylamine 100:50:1, gave the title compound (1.16 g, 81%) as an oil. [alpha]D +29.9 (c 2, MeOH), 87% ee. Recrystallisation of the (-)-(1R)-10-camphorsulfonate salt from ethyl acetate, and reliberation of the free-base, afforded the title compound with 98% ee, [alpha]D +33.7 (c 2, MeOH). IR numax 1728 cm-1; 1 H-NMR (CDCl3) delta1.54 (3H, d, J 6.5 Hz, CHCH3), 1.72 and 1.90 (12H, 2s, adamantyl CH2), 2.03 (3H, s, adamantyl CH), 5.88 (1H, q, J 6.5 Hz, CHCH3), 7.30 (1H, m, Py 5-H), 7.65 (1H, m, Py 4-H), 8.56 (1H, m, Py 6-H), 8.63 (1H, m, Py 2-H); MS m/z 285 (M+). Anal. Calcd: C, 75.76; H, 8.12; N, 4.91. Found: C, 75.30; H, 8.18; N, 4.46%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5096-11-7, (S)-1-(3-Pyridyl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; British Technology Group Limited; US5595995; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 936841-69-9, 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. 936841-69-9, name is 4-(Trifluoromethyl)picolinonitrile, molecular formula is C7H3F3N2, 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.

A solution of the product from Step B (1.3 g, crude) in a mixed solvent of HC1 (conc.) and dioxane (20 mL, 1:1) was refluxed for 2 hours. The mixture was concentrated to obtain the titleproduct (350 mg, 60% for 2 steps) as a brown solid which was used for the next step without any further purification. MS: MIe 192 (M+1).

According to the analysis of related databases, 936841-69-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BEIGENE, LTD.; ZHOU, Changyou; ZHANG, Guoliang; WO2014/206344; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 33252-28-7, 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. 33252-28-7, name is 6-Chloronicotinonitrile, molecular formula is C6H3ClN2, 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.

Step 1: 6-Isopropoxynicotinonitrile (48). To a stirring suspension of Potassium tert-butoxide (6.0 g, 54.12 mmol) in THF (200 mL) at 0 C. was added isopropanol (4.17 mL, 54.13 mmol) and the reaction mixture was stirred for 5 min. Compound 47 (5.0 g, 36.08 mmol) was added at 0 C. and the reaction mixture was stirred for 2 h at room temperature. The reaction mixture was concentrated in vacuo, the resulting residue was dissolved/suspended in water and extracted with EtOAc. The combined organic layers were washed with sat. NaCl, dried and concentrated to afford 48 (5.6 g) which was used as such for the next step.

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 33252-28-7, 6-Chloronicotinonitrile.

Reference:
Patent; Exelixis, Inc.; US2010/249071; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 135900-33-3, 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.135900-33-3, name is 6-(Trifluoromethoxy)pyridin-3-amine, molecular formula is C6H5F3N2O, molecular weight is 178.11, as common compound, the synthetic route is as follows.

A mixture of Example 235C (0.095 g, 0.350 mmol), PyBOP ((1H- benzo[(i] [l ,2,3]triazol-l-yl)oxy)tri(pyrrolidin-l-yl)phosphonium hexafluorophosphate(V)) (0.219 g, 0.420 mmol), 6-(trifluoromethoxy)pyridin-3-amine (0.075 g, 0.420 mmol), and triethylamine (0.073 mL, 0.525 mmol) in N,N-dimethylformamide (DMF) (3 mL) was stirred for 3 hours. The reaction mixture was quenched with brine and saturated NaHC(, and extracted with ethyl acetate (2x). The combined organic layers were washed with brine, dried over (1679) MgSO/t, filtered, and concentrated. The residue was purified on a 12 g column using the Biotage Isolera One flash system eluted with heptanes/ethyl acetate (7:3 to 6:4) to provide the title compound (65.1 mg, 43%). MS (ESI+) nt/z 432.3 (M+H)+.

Statistics shows that 135900-33-3 is playing an increasingly important role. we look forward to future research findings about 6-(Trifluoromethoxy)pyridin-3-amine.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; MURAUSKI, Kathleen; (288 pag.)WO2019/90074; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1256789-09-9, Adding some certain compound to certain chemical reactions, such as: 1256789-09-9, name is Methyl 6-chloro-2,4-dimethylnicotinate,molecular formula is C9H10ClNO2, 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 1256789-09-9.

a) Synthesis of 2-(methoxymethyl)-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid methylesterTo a solution of 710 mg, (3.6 mmol) 6-chloro-2,4-dimethyl-pyridine-3-carboxylic acid methylester in CCI4 (16 ml) were added 688 mg (3.90 mmol) N-bromosuccinimide, 59 mg (0.36 mmol) AIBN and 210 muIota (3.72 mmol) acetic acid . The reaction mixture was irradiated with a 200W Wolfram lamp at 60 C for 24 h. The mixture was then filtered through celite, washed with CCI4 and concentrated in vacuo. After CC (hexane/EtOAc 97:3) of the residue a mixture of 6-chloro-2,4-dimethyl-pyridine-3-carboxylic acid methylester, 4-(bromomethyl)-6- chloro-2-methyl-pyridine-3-carboxylic acid methylester and 2-(bromomethyl)-6-chloro-4- methyl-pyridine-3-carboxylic acid methylester was obtained. This mixture was dissolved in dioxane (10 ml) and added at 0 C to a solution prepared by dissolving 594 mg (25.8 mmol) sodium in MeOH (11 ml) at 0 C. This reaction mixture was stirred at RT for 3 h. Then the reaction solution was poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2S04 and concentrated in vacuo. After CC (hexane/EtOAc 97:3) of the residue again a mixture of 6-chloro-4-(methoxymethyl)-2-methyl- pyridine-3-carboxylic acid methylester and 6-chloro-2-(methoxymethyl)-4-methyl-pyridine-3- carboxylic acid methylester was obtained. This material was dissolved in NMP (7.8 ml) and 860 muIota (9.85 mmol) morpholine and 1.36 g (9.85 mmol) K2C03 were added followed by heating at 100 C for 5 h. Then the mixture was poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2S04 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 9:1) provided 90 mg (0.32 mmol, 9%) 2-(methoxymethyl)-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid methylester.

According to the analysis of related databases, 1256789-09-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GRUeNENTHAL GMBH; KUeHNERT, Sven; BAHRENBERG, Gregor; KLESS, Achim; SCHROeDER, Wolfgang; LUCAS, Simon; WO2012/52167; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 33252-28-7, Adding some certain compound to certain chemical reactions, such as: 33252-28-7, name is 6-Chloronicotinonitrile,molecular formula is C6H3ClN2, 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 33252-28-7.

Example 29Step A6-Bromonicotinonitrile. 6-Chloronicotinonitrile (13.8 g, 100 mmol) was heated at 145 C in phosphorus tribromide (150 ml.) for 32 h. After cooling, the mixture was concentrated in vacuo. To the residue was added phosphorus tribromide (150 ml_), and the mixture was heated at 145 C for another 32 h. After cooling, the mixture was concentrated in vacuo, and an ice-water mixture (500 ml.) was added. Sodium bicarbonate was added to neutralize the mixture, and the product was extracted with ethyl acetate (3 chi 250 ml_). The combined organic extracts were washed with brine and dried over magnesium sulfate. The solvent was removed in vacuo, and the residue was chromatographed (hexanes-ethyl acetate) to give 14.9 g (81 %) of 6-bromonicotinonitrile as a white solid: 1 H NMR (400 MHz, CDCI3) S 7.66 (d, J = 1 1.0 Hz, 1 H), 7.80 (dd, J = 3.1 , 1 1.0 Hz, 1 H), 8.67 (d, J = 3.1 Hz, 1 H); MS (M+H)+ m/z=183.0, 185.0.

According to the analysis of related databases, 33252-28-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; BURGESS, Gary; WO2012/114223; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 135900-33-3, 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. 135900-33-3, name is 6-(Trifluoromethoxy)pyridin-3-amine, molecular formula is C6H5F3N2O, 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.

A solution of Br2 (0.25 mL, 4.87 mmol) in HO Ac (3 mL) was added dropwise to a stirring solution of 6-(trifluoromethoxy)pyridin-3-amine (400 mg, 2.25 mmol) in EtOH (15 mL) and HO Ac (1.5 mL) at 0C under a nitrogen atmosphere. After addition was complete, the reaction was warmed to room temperature and was allowed to stir for an additional 15 hours. The reaction mixture was concentrated. DCM (30 mL) and saturated aqueous NaHC03 (20 mL) were added to the crude residue. The aqueous layer was extracted with DCM (50 mL x 3). The combined organic layers were dried over Na2S04, filtered and concentrated. The crude residue was purified by column chromatography (0-10% EtOAc in petroleum ether) to give 2,4- dibromo-6-(trifluoromethoxy)pyridin-3-amine (670 mg, yield: 89%) as light yellow solid. 1H NMR (400 MHz, CDCl3): d = 7.18 (s, 1H), 4.59 (s, 2H).

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 135900-33-3, 6-(Trifluoromethoxy)pyridin-3-amine.

Reference:
Patent; GENENTECH, INC.; STAFFORD, Jeffrey, A.; VEAL, James, M.; TRZOSS, Lynnie, Lin; MCBRIDE, Christopher; PASTOR, Richard, M.; STABEN, Steven, Thomas; STIVALA, Craig; VOLGRAF, Matthew; (200 pag.)WO2020/18970; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 53344-73-3, name is 2-Chloro-4,4′-bipyridine, the common compound, a new synthetic route is introduced below. Formula: C10H7ClN2

A mixture of 1.3 g of 2-chloro-4,4′-bipyridine and 6.5 ml of anhydrous hydrazine in 40 ml of dry pyridine was refluxed for 24 hours under argon and then concentrated. The residue was dissolved in methylene chloride, treated with activated carbon and the solvent was removed giving an oil which was crystallized from ether-hexane-methylene chloride. A 1.3 g portion of these crystals of 2-hydrazino-4,4′-bipyridine was combined with 50 ml of triethyl orthoacetate and heated on a steam bath for 1 hour. After standing overnight, hexane was added and after further standing, crystals separated. These crystals were collected and recrystallized from acetonehexane, giving the desired product as off-white crystals, mp 223-226 C.

The synthetic route of 53344-73-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US4550166; (1985); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1137-67-3, 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 1137-67-3, name is 2-(Pyridin-3-yl)-1H-benzo[d]imidazole. This compound has unique chemical properties. The synthetic route is as follows.

A reaction mixture of NiSO4·6H2O (0.0260 g, 0.1 mmol), 3PBI (0.0195 g, 0.1 mmol),NaOH (0.0072 g, 0.18 mmol), ADP (0.0146 g, 0.1 mmol), and water (6 mL) was added toa 15-mL Teflon reactor and heated under autogenous pressure at 160 C for 3 days. The reaction mixture was cooled to room temperature at a rate of 5 C h-1. Green pellet crystalsof 1 suitable for X-ray diffraction analysis were obtained (0.032 g, yield: 48.01% based on NiSO4). Elemental analysis Calcd (%) for C30H34NiN6O8 (665.34): C, 54.16; H, 5.15; N,12.63; found: C, 54.40; H, 5.17; N, 12.57; IR (KBr, cm-1): 3359(w), 3203(w), 2926(w),2220(br), 1552(s), 1448(m), 1404(s), 1313(s), 1286(m), 1286(m), 1226(m), 1195(m), 1128(m), 1055(w), 1028(w), 1001(w), 962(m), 735(s), 690(m), 432(m), 408(w).

According to the analysis of related databases, 1137-67-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Cui-Cui; Wang, Jin-Hua; Tang, Gui-Mei; Wang, Yong-Tao; Cui, Yue-Zhi; Ng, Seik Weng; Journal of Coordination Chemistry; vol. 68; 21; (2015); p. 3918 – 3931;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 716362-10-6, 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 716362-10-6, name is 6-Chloro-4-methoxynicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

A suspension of 6-chloro-4-methoxynicotinic acid (12 g, 64 mmol) in 50C12 (60 ml) was refluxed for 4 hours. The resulting solution was concentrated under vacuum, and the residue was azeotroped with toluene (30 ml) to afford a yellow solid, which was added intotBuOH (50 ml) and stirred at room temperature overnight. The reaction mixture partitioned between aq.NaOH (200 ml, 5%) and DCM (100 mL), and the aq. phase was extracted with DCM (2 x 100 mL). The organic layers were washed with brine (100 mL), dried over Na2504 and concentrated to afford tert-butyl 6-chloro-4-methoxynicotinate as yellow solid. ?H NIVIR(CDC13, 400 IVIHz) 8.60 (s, 1H), 6.87 (s, 1H), 3.92 (s, 3H), 1.54 (s, 9H). LC/MS (m/z): 244(M+H).

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 716362-10-6, 6-Chloro-4-methoxynicotinic acid.

Reference:
Patent; MERCK SHARP & DOHME CORP.; UJJAINWALLA, Fez; TAN, John Qiang; DANG, Qun; SINZ, Christopher J.; WANG, Ming; CHEN, Yili; CAI, Jiaqiang; DU, Xiaoxing; (41 pag.)WO2016/54806; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem