Pyridine-derivatives

Electric Literature of 67515-76-8, 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. 67515-76-8, name is Methyl 5-aminopicolinate, molecular formula is C7H8N2O2, 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 62 Preparation of methyl 5-fluoropicolinate STR225 The methyl 5-aminopicolinate (2.2 g) is dissolved in 5.5 ml 48% fluoroboric acid and 20 ml 95% ethanol. This mixture is cooled, with stirring, to -3 C. and then 1.81 g n-butyl nitrite added dropwise. After a further one-half hour at -3 C., 0.5 ml n-butyl nitrite is added slowly and stirring continued for one-half hour at 0 C. After adding 20 ml ether carefully, the mixture is rapidly filtered, and the solid washed twice with cold hexane. The solid is suspended in 100 ml heptane, and the suspension slowly heated with stirring. At about 60 C., a vigorous exothermic reaction occurs. Heating is then continued to 80 C. A red oil separates on the sides of the flask. The heptane solution is filtered, and the filtrate concentrated to give the desired product. The red oil is dissolved in water, excess sodium bicarbonate solution added, and the solution extracted with ethyl acetate. The ethyl acetate extract is washed with saturated brine, dried and concentrated. The residue is chromatographed on silica gel and the product, methyl 5-fluoropicolinate, eluted with 1:1-ether:hexane. This material is used directly for the preparation of the picolinic acid.

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 67515-76-8, Methyl 5-aminopicolinate.

Reference:
Patent; American Cyanamid Company; US4638068; (1987); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 53014-84-9, 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.53014-84-9, name is 2-Methyl-5-formylpyridine, molecular formula is C7H7NO, molecular weight is 121.1366, as common compound, the synthetic route is as follows.

154. (+)-2- 3,4-trans)-4-methyl-l-g6-methylpyridin-3- yl)methyl)pyrrolidin-3-yl)-7-ftetrahvdro-2H-pyran-4-yl)imidazo[5,l- f] ri,2,41triazin-4(3H)-one [1113] To a stirred solution of (-)-2-((3,4-trans)-4-methylpyrrolidin-3-yl)-7- (tetrahydro-2H-pyran-4-yl)imidazo[5,l- J[l,2,4]triazin-4(3H)-one (150 mg, 0.49 mmol) in MeOH (10 mL) was added 6-methylnicotinaldehyde (71 mg, 0.59 mmol) at room temperature and stirred for 2 h under argon atmosphere. To the resulting solution was added NaCNBH3 (93 mg, 1.48 mmol) and stirring was continued for another 8 h at room temperature. The volatiles were evaporated under reduced pressure. The residue was diluted with water and extracted with CH2CI2 (2 x 20 mL). Combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified by silica gel column chromatography to afford (+)-2-((3,4-trans)-4-methyl-l-((6-methylpyridin-3- yl)methyl)pyrrolidin-3-yl)-7-(tetrahydro-2H-pyran-4-yl)imidazo[5, 1 -f [ 1 ,2,4]triazin- 4(3H)-one (43 mg, 21%) as an off-white solid. 1H-NMR (DMSO-d6, 400 MHz): delta 8.38 (s, 1H), 7.67 (s, 1H), 7.58 (d, 1H), 7.21 (d, 1H), 3.97-3.91 (m, 2H), 3.64-3.59 (m, 2H), 3.52-3.49 (m, 1H), 2.94-2.92 (m, 1H), 2.87-2.84 (m, 2H), 2.79-2.71 (m, 2H), 2.67-2.61 (m, 2H), 2.42 (s, 3H), 2.24-2.21 (m, 1H), 1.87-1.82 (m, 4H), 1.09 (d, 3H); Mass (ESI): 409.3 [M++l]; LC-MS: 96.82%; 409.4 (M++l); (column; Eclipse XDB C-18, (150×4.6 mm, 5.0mu); RT 5.58 min. 0.05% TFA (Aq): ACN; 1.0 ml/min); UPLC (purity): 98.45%; (column; Acquity UPLC HSS-T3, 100×2.1 mm, 1.8mu; RT 2.83 min. 0.025% TFA (Aq): ACN; 0.30 ml/min; Chiral HPLC: 99.61%, R,= 9.69 min (Chiralpak IA, 250 x 4.6mm, 5mu; mobile phase (A) 0.1% DEA in n-Hexane (B) DCM:MeOH (80:20) (A: B : 80:20); flow Rate: 1.00 mL/min); Optical rotation [a]D20: + 18.96 (c = 0.25, DCM). TLC: 5% MeOH/DCM (Rf: 0.3).

The chemical industry reduces the impact on the environment during synthesis 53014-84-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13534-98-0, 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 13534-98-0, name is 4-Amino-3-bromopyridine. This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of 3-Prop-1-ynyl-pyridin-4-ylamine (LXXIII). To a solution of LXXII (1.5 g, 8.67 mmol) in N,N-dimethyl formamide (20 mL) was added solid sodium acetate (2.1 g, 0.02106 mol). The resulting mixture was degassed for 10 min and then [1,1?- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.31 g, 0.430 mmol), followed by tributyl(prop-1-yn-1-yl)stannane (3.7g, 11.3 mmol), were added. The reaction mixture 25 was heated at 100 C in a sealed tube for 12 h, before being allowed to cool to room temperature. The reaction mixture was poured in to water and the mixture was extracted 157 of 363 {//– DRAFT –//4069/3020WO/00228726/v2} 4069.3020 WO with ethyl acetate (3 x 50 mL). The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. The crude product mixture was purified by column chromatography on (100-200 mesh) silica, using 3% methanol in dichloromethane as the eluant to afford LXXIII (1 g, 87%) as a semi solid.1H NMR (400 MHz, CDCl3) delta 8.29 5 (s, 1H), 8.08 (d, 2H, J= 5.7 Hz), 6.50 (d, 2H, J= 5.6 Hz), 4.61 (brs, 2H), 2.11 (s, 3H); MS (ESI, positive mode) m/z 133 (MH+).

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 13534-98-0, 4-Amino-3-bromopyridine.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; CULLEN, Matthew; HAUCK, Sheila; GENG, Bolin; FOLEY, Megan; BASTOS, Cecilia, M.; MUNOZ, Benito; HAEBERLEIN, Markus; WO2015/73528; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 70298-88-3, 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 70298-88-3 as follows.

To a solution of 2.67 g (15.0 mmol, 1 eq.) of pivalamide IV and 6.8 mL (45.0 mmol, 3 eq.) of TMEDA in 120 mL of dry diethylether, cooled to -78C, were added 18.0 mL (45.0 mmol, 3 eq., 2.5 M in hexane) of BuLi. After 15 minutes, the solution was brought back to -24C and stirred 2 hours. Then, the mixture was cooled down to – 78C before addition of 4.0 mL (33.0 mmol, 2.2 eq) of p-anisaldehyde in 60 mL of THF. The reaction was brought back to 0C and stirred 2 hours before being stirred at room temperature over night. Then, 120 mL of water were added. The aqueous layer was extracted with 2 x 80 mL of dichloromethane. The organic phase was dried, filtered and concentrated. The crude mixture was purified over silicagel. The obtained white solid (estimation 9 mmol of XII) was dissolved in 90 mL of DCM. Then, 7.74 g (89.0 mmol, 10 eq.) of activated Mn02 were added and the reaction was refluxed 20 hours. The reaction was brought back to room temperature and 7.74 g (89.0 mmol, 10 eq.) of activated Mn02 were added again. After 20 hours to reflux, the mixture was filtered on celite and the solvent was evaporated. The crude mixture was dissolved in 180 mL of 3 M aqueous HCI were added and refluxed 16 hours. The reaction was cooled down to 0C and 50 mL of aqueous ammonia were added. The aqueous layer was extracted with 3 x 90 mL of DCM. The organic phase was dried, filtered and concentrated. Purification over silica gel afforded 1.65 g (7.2 mmol, 48%) of XIII as a yellow solid. The yield varied from 38% to 48%. Rf=0.15 (PE/EtOAc 1 :2). 1H NMR (300 MHz): delta = 8.26 (s, 1 H), 7.94 (d, J = 5.1 Hz, 1 H), 7.72 (m, 2 H), 7.22 (m, 1 H), 6.96 (d, J = 5.1 Hz, 2 H), 5.58 (s, 2 H), 3.88 (s, 3 H) ppm. 13C NMR (75 MHz): delta = 196.5, 163.4, 144.0, 141.1 , 137.1 , 132.2, 130.6, 124.7, 123.4, 1 13.8, 55.6 ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,70298-88-3, its application will become more common.

Reference:
Patent; LYTIX BIOPHARMA AS; STENSEN, Wenche; SCHEVENELS, Florian; MARKO, Istvan, E.; SVENDSEN, John, Sigurd, Mj°en; WO2014/198848; (2014); A2;,
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. 5632-81-5, name is 2-Chloropyridine-3,5-diamine, molecular formula is C5H6ClN3, 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. category: pyridine-derivatives

80 ml of ethanol are placed in a 250-ml one-necked round-bottomed flask equipped with a calcium chloride guard tube, followed by addition, with stirring, of 4.11 g (18.1 mmol) of 2-(propan-2-yloxy)pyrazolo[l,5-a]pyridin-3-amine hydrochloride. 1.18 g (8.21 mmol) of 2-chloropyridine-3,5-diamine and 5.0 ml (29 mol) of N-ethyl-N-(propan-2-yl)propan-2-amine are added to this solution.The solution is then stirred at room temperature for 4 days. The black precipitate formed is isolated by filtration, washed with water and dried in a desiccator under vacuum at 30C in the presence of a desiccant, to constant weight. The compound is thus obtained in the form of a black powder.

With the rapid development of chemical substances, we look forward to future research findings about 5632-81-5.

Reference:
Patent; L’OREAL; FADLI, Aziz; BLAIS, Stephane; (70 pag.)WO2016/97198; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 68325-15-5, 3-Chloro-4-cyanopyridine, 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: C6H3ClN2, blongs to pyridine-derivatives compound. HPLC of Formula: C6H3ClN2

Intermediate 1 : lsoxazolo[5,4-c1pyridin-3-ylamine.; To a solution of 3-chloro-isonicotinitrile (1.13 g, 8.36 mmol) in DMF (6.0 mL) were added potassium carbonate (1.69 g, 12.2 mmol) and acetohydroxamic acid (0.91 g, 12.2 mmol). The reaction mixture was stirred at rt overnight, diluted with EtOAc (200 mL) and extracted with saturated aqueous NaHCO3 (200 mL) then saturated aqueous NaCI (100 mL). The aqueous layers were back extracted with EtOAc (200 mL) and the combined organic layers were dried (MgSO4) and concentrated. The crude residue was purified (FCC, 2 N NH3 in MeOH/DCM) to give isoxazolo[5,4-c]pyhdin-3-ylamine (0.447 g, 41 %). MS (ESI+): calcd for C6H5N3O m/z 135.04, found 136.2 (M+H)+. 1H NMR (d6-DMSO): 8.93 (d, J = 0.8, 1 H), 8.45 (d, J = 5.2, 1 H), 7.88-7.86 (dd, J = 5.2, 1.2, 1 H), 6.72 (br s, 2H).

The synthetic route of 68325-15-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BREITENBUCHER, J., Guy; KEITH, John, M.; TICHENOR, Mark, S.; CHAMBERS, Alison, L.; JONES, William, M.; HAWRYLUK, Natalie, A.; TIMMONS, Amy, K.; MERIT, Jeffrey, E.; SEIERSTAD, Mark, J.; WO2010/68453; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 15854-87-2, 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 15854-87-2, name is 4-Iodopyridine. This compound has unique chemical properties. The synthetic route is as follows.

The intermediates and final products were obtained via establishedcross-coupling reactions [5,15,17]. Briefly, 4-trimethylsililyethynylpyridine was obtained by reacting an equimolarquantity of 4-iodopyridine (2.0 mmol) with trimethylsilylethyne(TMSE, 2.0 mmol) in THF/iPrNH2 using Pd(II)/Cu(I) catalysts(Scheme 1). The crude product obtained was purified by silicacolumn chromatography using hexane/dichloromethane eluantsystems. This was followed by a protodesilylation reaction underbasic condition (aq. KOH in MeOH/THF) and the 4-ethynylpyridinewas separated by silica column chromatography using puredichloromethane as eluant. In the next phase of the reaction,respective aryl halides (2.0 mmol) and 4-ethynylpyridine (2.0mmol) were coupled via a Sonogashira cross-coupling reaction.Final products were purified using an alumina column and obtainedas tan to light brown solid in quantitative yields.

According to the analysis of related databases, 15854-87-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Haque, Ashanul; Al Balushi, Rayya A.; Al-Busaidi, Idris Juma; Ilmi, Rashid; Al Rasbi, Nawal; Jayapal, Maharaja; Khan, Muhammad S.; Raithby, Paul R.; Journal of Organometallic Chemistry; vol. 892; (2019); p. 75 – 82;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 21543-49-7, 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. 21543-49-7, name is 2-Chloro-5-hydroxymethylpyridine, molecular formula is C6H6ClNO, 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 solution of 2-chloro-5-hydroxymethylpyridine (0.45 g, 0.003 mole) in DCM (10 mL) at 0 C under N2, was added phosphorus tribromide (0.44 mL, 0.0037 mole) drop wise. Reaction mixture was warmed to RT and stirred for 1.5 hours. The reaction mixture was diluted with DCM (75 mL), treated with saturated aqueous sodium bicarbonate (20 mL). Organic layer was washed with water (20 mL), brine solution (20 mL) and dried over Na2S04 and concentrated under vacuum to obtain the title compound. Yield: 0.49 g; lH – NMR (CDC13, 400 MHz) delta ppm: 4.35 (s, 2H), 7.32 – 7.34 (d, J = 8.2 Hz, 1H), 7.69 – 7.71 (dd, J = 2.2, 7.9 Hz, 1H), 8.40 – 8.41 (d, J = 1.7 Hz, 1H); Mass (m/z): 205.9, 208.0 (M+H)+.

According to the analysis of related databases, 21543-49-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; SHINDE, Anil Karbhari; MOHAMMED, Abdul Rasheed; BADANGE, Rajesh Kumar; JAYARAJAN, Pradeep; BHYRAPUNENI, Gopinadh; JASTI, Venkateswarlu; (172 pag.)WO2018/42362; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 524955-09-7, 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. 524955-09-7, name is 3-Chloro-4-(pyridin-2-ylmethoxy)aniline, molecular formula is C12H11ClN2O, 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.

Following hydrogenation to form the first aniline intermediate, acid catalyzed coupling was performed to prepare 4-[3-chloro-4-(2-pyridylmethoxy)anilino]-3-cyano-7-ethoxy-6-N-acetylaminoquinoline, as shown below: To perform the coupling reaction, the two reactants were heated together in alcohol at 65-78 C. over 4-6 hours, yielding the product. The reaction begins as an amber slurry and thickens to a lighter beige slurry as it approaches completion. Upon scaling up from 75 g to 350 g, it proved necessary to add a catalytic amount (0.025 eq.) of methanesulfonic acid to initiate the reaction. As a specific example, 4-chloro-3-cyano-7-ethoxy-6-N-acetylaminoquinoline (0.141 kg, 0.49 mole) was added to the mixture of Example 2, followed by ethanol (0.037 L) to give a suspension. A catalytic amount of methanesulfonic acid (1.17 g) was added at 20-25 C. The resulting slurry was heated to 70-75 C. and held for a minimum of 4 hours. Thickening of the slurry was evident after 1.5 hours. Following reaction completion, the mixture was cooled to room temperature and may be used ?as is? in the telescoped reaction of Example 4 below.; As solvents EtOH, DMF or other suitable solvent may be used. Experimental results obtained using different solvents and reaction conditions are shown in Table 3. Difficulty filtering the product of this step (noted in several entries on Table 3) was circumvented by not isolating the solid at this point, but telescoping the reaction with the next step. It has been found that on the order of 20 volumes of EtOH were necessary to achieve reasonable stirring, but that the reaction can proceed in only 10 volumes of DMF, without significant loss in purity. In Table 3, where the entry is labelled NI, the intermediate product was not isolated, but carried into the next reaction step. TABLE 3 Coupling Reaction Coupling Temp Time Yield Solvent Solvent ( C.) (h) (%) Comments IPA EtOH 78 4 85.4 contains impurity THF EtOH 78 4 90.5 v. slow filtration THF THF 68 4 NA Only 16% product formed THF EtOH 78 4 94.2 v. slow filtration EtOH IPA 82 5 NA No reaction EtOH MeOH 65 5 60.0 v. slow filtration THF EtOH 78 1.5 80.3 v. slow filtration (MeSO3H) THF EtOH 78 4 86.0 v. slow filtration THF EtOH 78 3 85.7 4 h filtration – hard, green (MeSO3H) coated solid on drying THF Dimethoxy 85 2 74.2 Faster filtration (<1 hr) ethane Nice yellow solid THF Diethoxy 85 5 - - Methane THF Dimethoxy 70 6 - - Ethane THF EtOH 78 6 96.6 Slow filtration THF DMF 78 0.5 65.6 Some product lost in filtrate (MeSO3H) THF DMF 70 8 NI See Note 1 (MeSO3H) THF EtOH 78 6 ND See Note 2 (MeSO3H) THF EtOH 78 4 NI Yield to the free base is (MeSO3H) 80.4%3/ THF EtOH 75 4 NI Yield to the free base is (MeSO3H) 83%3/ THF EtOH 75 4 NI Yield to the free base is (MeSO3H) 86%3/ NR = no reaction, NI = not isolated; ND = not determined; NA = not available 1. Carried through to the deprotection and generation of free base to give 69.5% overall yield. 2. The overall yield after the deprotection and generation of the free base is 76.1% 3This reaction was not filtered at all but taken as slurry to 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 524955-09-7, 3-Chloro-4-(pyridin-2-ylmethoxy)aniline. Reference:
Patent; WYETH; US2006/270668; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 65753-47-1, Adding some certain compound to certain chemical reactions, such as: 65753-47-1, name is 2-Chloro-3-(trifluoromethyl)pyridine,molecular formula is C6H3ClF3N, 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 65753-47-1.

2-Chloro-3-trifluoromethyl-pyridine (3 g, 16.53 mmol) was dissolved in 30ml of a solution of sodium methoxide (5.4M) in methanol. The mixture was stirred at ambient temperature for 2 days. After this period of time, the reaction was taken into ice and extracted with DCM three times. The combined extract was washed with brine, dried over magnesium sulfate and concentrated in vacuo to give 2-methoxy-3-trifluoromethyl-pyridine as a light liquid (2.7 g, 89% yield). 1 H-NMR (400 MHz, DMSO-d6, 298 K): ? ppm 3.98 (s, 3H) 7.2 (dd, 1 H) 8.1 1 (d, 1 1-1) 8.45 (d, 1 H). MS: 178.1 [M+1 ]+, Rt(1) =1 .29 min.

According to the analysis of related databases, 65753-47-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; LEWIS, Ian; SMITH, Alexander, Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; WOLF, Romain; ZECRI, Frederic; WO2013/57711; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem