Month: July 2021

Synthetic Route of 154048-89-2 , The common heterocyclic compound, 154048-89-2, name is N-Boc-3-Amino-4-iodopyridine, molecular formula is C10H13IN2O2, 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.

A resealable pressure vessel was charged with tert-butyl tert-butyl (4-iodopyridin-3-yl)carbamate (1.54 g, 4.8 mmol), ((prop-2-yn-1-yloxy)methyl)benzene (0.84 g, 5.8 mmol), bis(triphenylphosphine) palladium(II) chloride (0.17g, 0.24 mmol), copper(I) iodide (0.09 g, 0.48mmol), triethylamine (15 mL, 108 mmol) and DMF (5 mL). The mixture was degassed by bubbling nitrogen through for several minutes, the flask was sealed and the reaction mixture was stirred for 7h.. The mixture was diluted with EtOAc and washed with saturated ammonium chloride (2x) and brine (1x). The organics were dried over sodium sulfate, filtered and evaporated, and the crude material purified by silica gel chromatography, eluting with 12-100% EtOAc in hexanes, affording tert-butyl (4-(3-(benzyloxy)prop-1-yn-1-yl)pyridin-3-yl)carbamate (1.6 g, 98%). 1H NMR (400MHz, CHLOROFORM-d) delta = 9.44 (s, 1H), 8.28 (d, J=4.8 Hz, 1H), 7.45 – 7.33 (m, 5H), 7.26 (d, J=4.8 Hz, 1H), 7.14 – 6.93 (m, 1H), 4.71 (s, 2H), 4.50 (s, 2H), 1.56 (s, 9H).

The synthetic route of 154048-89-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; McDonald, Ivar M.; Mate, Robert; Ng, Alicia; Park, Hyunsoo; Olson, Richard E.; Tetrahedron Letters; vol. 59; 8; (2018); p. 751 – 754;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 885588-12-5, Adding some certain compound to certain chemical reactions, such as: 885588-12-5, name is 2-Bromo-5-fluoro-4-pyridinecarboxylic acid,molecular formula is C6H3BrFNO2, 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 885588-12-5.

To a solution of 2-bromo-5-fluoroisonicotinic acid (3.0 g, 13.64 mmol) in EtOH (30 mL) was added EtONa (3.7 g, 54.55 mmol). The reaction was heated at 60 00 for 24 hours then cooled to room temperature and thionyl chloride (3.2 g, 27.28 mmol) added dropwise. Thereaction was stirred at room temperature overnight then the solvent removed. The residue was partitioned between DOM (20 mL) and water (10 mL) and the aqueous phase extracted with DOM (3 x 10 mL). The combined organic extracts were washed with a saturated aqueous NaHCO3 solution (3 x 10 mL), brine (3 x 10 mL), dried (Na2SO4), filtered and concentrated. The residue obtained was purified by column chromatography(EtOAc/petroleum ether=1/20 v/v) to give the title compound (2.1 g, 56%) as an off-white solid. 1H-NMR (400MHz, ODd3) 6 8.14 (s, 1 H), 7.69 (s, 1 H), 4.40-4.35 (q, J = 7.2 Hz, 2H), 4.21-4.15 (q, J= 6.8 Hz, 2H), 1.46 (t, J= 7.2 Hz, 3H), 1.38 (t, J= 7.2 Hz, 3H); LOMS RT2.61 mm; m/z 274, 276 [M+H].

According to the analysis of related databases, 885588-12-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CTXT PTY LIMITED; BERGMAN, Ylva Elisabet; CAMERINO, Michelle Ang; STUPPLE, Paul Anthony; (81 pag.)WO2017/153520; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 7464-14-4, 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.7464-14-4, name is 2-Hydroxy-5-methyl-3-nitropyridine, molecular formula is C6H6N2O3, molecular weight is 154.12, as common compound, the synthetic route is as follows.

(Reference Example 5-1) At room temperature, to a mixed solvent solution of 5-methyl-3-nitropyridin-2-ol (5.0 g) in tetrahydrofuran (200 ml) and methanol (200 ml) was added 10% palladium carbon (0.5 g), followed by stirring for 24 hours under a hydrogen atmosphere. The reaction solution was filtered through Celite, and then the filtrate was concentrated under reduced pressure to afford 3-amino-5-methylpyridin-2-ol (4.03 g). 1H NMR (400 MHz, CDCl3) delta: 2.03(s, 3H), 4.11 (br s, 2H), 6.53 (s, 1H), 6.59 (s, 1H), 12.21 (br s, 1H).

Statistics shows that 7464-14-4 is playing an increasingly important role. we look forward to future research findings about 2-Hydroxy-5-methyl-3-nitropyridine.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2471792; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 5346-38-3 ,Some common heterocyclic compound, 5346-38-3, molecular formula is C6H6N2S, 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.

To 25 mL N,N-dimethyl formamide (DMF) containing alpha-b r omo a c e t o p heno n e ( 1 . 1 g , 5 . 5 m m o l ) , 2-pyridinecarbothioamide (760 mg, 5.5 mmol) was added.After kept stirring for 24 h, the reaction mixture was diluted with 200 mL EtOAc followed by washing with brine. Theorganic layer was dried over anhydrous Na2SO4 and evaporatedunder reduced pressure. Separation through flash columnchromatography using a mixture of n-hexane andEtOAc as eluents provided a white solid as the product. Yield: 81.0 %. Mp: 72-73 C. IR (film, cm-1): 3111, 3057,1576, 1499, 1462, 1461, 1273, 1240, 1065, 993, 781, 740,683. 1H NMR (CDCl3, 300 MHz, ppm) delta = 7.37-7.39 (m,2H), 7.46-7.51 (m, 2H), 7.63 (s, 1H), 7.83-7.88 (m, 1H), 8.03(d, 2H, J = 7.0 Hz), 8.36 (d, 1H, J = 7.8 Hz), 8.58 (d, 1H,J = 4.6 Hz).13C NMR (CDCl3, 75 MHz, ppm) delta = 115.3,119.9, 124.5, 126.4, 128.2, 128.8, 134.5, 137.1, 149.5,151.5, 156.7, 168.8. Anal. Calcd. (%) for C14H10N2S: C70.56, H 4.23, N 11.76. Found: C 70.48, H 4.31, N 12.01.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5346-38-3, its application will become more common.

Reference:
Article; Yang, Ming-Yang; Zhao, Xiao-Long; Zheng, Ming-Hua; Wang, Yue; Jin, Jing-Yi; Journal of Fluorescence; vol. 26; 5; (2016); p. 1653 – 1657;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2002-04-2, 5-(Pyridin-4-yl)-1,3,4-thiadiazol-2-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, 2002-04-2, blongs to pyridine-derivatives compound. name: 5-(Pyridin-4-yl)-1,3,4-thiadiazol-2-amine

A solution of (i?)-3-methoxy-4-(l-phenyl-2-((triisopropylsilyl)oxy)ethoxy)benzoic acid (0.1.0 g, 2.2 mmol, 1 eq.), 5-(4-pyridyl)-l,3,4-thiadiazol-2-yl amine (0.467g, 2.6 mmol, 1.2 eq.), HATU (1.35 g, 3.5 mmol, 1.5 eq.) and diisopropylethylamine (480 mu^, 2.75 mmol, 1.2 eq.) in NMP (10 mL) was stirred at 70 C for 16 hours. The cooled reaction mixture was added to water (100 mL) and the crude product filtered and partitioned between dichloromethane (100 mL) and water (15 mL). The layers were separated and the aqueous extracted with a mixture of dichloromethane (100 mL) and methanol (10 mL). The combined extracts were dried with magnesium sulfate, evaporated in vacuo and purified by silica gel column chromatography using a 20 – 100 % ethyl acetate in iso- exane gradient to afford (R)-3 -methoxy-4-(l -phenyl-2-((triisopropylsilyl)oxy)ethoxy)-N-(5-(pyridin-4-yl)- l,3,4-thiadiazol-2-yl)benzamide as a white solid (0.784 g, 60% yield). NMR (400 MHz, DMSO) 13.16 (IH, s), 8.79 (2H, dd, J=1.6, 4.5 Hz), 7.99 (2H, dd, J=1.6, 4.4 Hz), 7.84 (IH, d, J=2.0 Hz), 7.68 (IH, dd, J=2.1, 8.6 Hz), 7.52 – 7.48 (2H, m), 7.40 (2H, dd, J=7.6, 7.6 Hz), 7.37 – 7.32 (IH, m), 7.09 (IH, d, J=8.9 Hz), 5.62 (IH, dd, J=4.5, 6.5 Hz), 4.14 (IH, dd, J=6.8, 10.6 Hz), 4.00 (IH, dd, J=4.5, 10.8 Hz), 3.97 (3H, s), 1.15 – 1.08 (3H, m), 1.07 – 1.02 (18H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2002-04-2, its application will become more common.

Reference:
Patent; GENKYOTEX SA; MACHIN, Peter; SHARPE, Andrew; LOCK, Christopher James; CHAMBERS, Mark S; HODGES, Alastair; ALLEN, Vivienne; ELLARD, John M; (189 pag.)WO2016/98005; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 116632-24-7, 2-Amino-4,6-dichloropyridine, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

A mixture of 4,6-dichloropyridin-2-amine (2.0 g, 12.3 mmol), ethynylbenzene (2.51 g, 24.5 mmol), copper(I) iodide (234 mg, 1.23 mmol), Dichlorobis(triphenylphosphine)- palladium(II) (1.0 g, 1.23 mmol) and triethylamine (4.3 ml, 31 mmol) is stirred under argon atmosphere in ACN (20 ml) with THF (10 ml) for 6 h at 90C. The mixture is diluted with water and extracted with EtOAc. The combined organic layers are dried over MgS04, concentrated in vacuo and the product purified by NP chromatography. Yield: 1.2 g (43%). HPLC-MS: M+H=229; tR=l .96 min (*Method_2).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,116632-24-7, 2-Amino-4,6-dichloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; REISER, Ulrich; BADER, Gerd; SPEVAK, Walter; STEFFEN, Andreas; PARKES, Alastair L.; WO2013/127729; (2013); 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. 5470-70-2, name is Methyl 6-methylnicotinate, molecular formula is C8H9NO2, 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. Product Details of 5470-70-2

250mL single-neck flask was added methyl 6-methylpyridine-3-carboxylate (10g, 66.15mmol) and 1,4-dioxane (100mL), was added under stirring selenium dioxide (14.7g, 132mmol), nitrogen heated to 85 under the protection of the reaction overnight. Cooling to room temperature, filtered, and the solvent was removed by rotary evaporation, the crude product was purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v) = 1/1), give a pale yellow solid 1.6g, Yield: 15percent.

With the rapid development of chemical substances, we look forward to future research findings about 5470-70-2.

Reference:
Patent; Guangdong East Sunshine Pharmaceutical Co., Ltd.; Wang, Xiaojun; Yang, Xinye; Zhou, Pingjian; Yang, Chuanwen; Lin, Jihua; Xiong, Shaohui; Zhang, Yingjun; Xiao, Ying; Wang, Hui; Cao, Shengtian; Wu, Fangyuan; Ouyang, Luo; (74 pag.)CN105524053; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 133081-24-0, Adding some certain compound to certain chemical reactions, such as: 133081-24-0, name is 6-Hydrazinylnicotinic acid,molecular formula is C6H7N3O2, 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 133081-24-0.

A solution of DOTA tri-t-butyl ester (225 mg, 0.393 mmol), HOBt (50 mg, 0.33 mmol), and EDC (62 mg, 0.32 mmol) in 50:50 dichloromethane:acetonitrile (2.0 mL) was stirred at ambient temperatures under nitrogen for 5 minutes, and treated with 6-hydrazinictoic acid (50 mg, 0.32 mmol). The solution was stirred for 60 hours and concentrated under reduced pressure. The residue was purified by HPLC on a Phenomenex Luna Cl 8 column (21.2 x 250 mm) using a 0.9%/min gradient of 9 to 36% acetonitrile containing 0.1% TFA at a flow rate of 20 niL/min. The main product peak eluting at 32.9 minutes was lyophilized to give the title compound as an off-white solid (3.0 mg, 1.0%). MS (ESI): 708.4 (60, M+H).

According to the analysis of related databases, 133081-24-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB PHARMA COMPANY; WO2007/5491; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 5470-70-2, 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.5470-70-2, name is Methyl 6-methylnicotinate, molecular formula is C8H9NO2, molecular weight is 151.16, as common compound, the synthetic route is as follows.

[01 10j To a solution of methyl 6-methylnicotinate (0.5 g, 3.31 mmol) in carbon tetrachloride (15 mL) was added N-bromosuccinimide (0.647 g, 3.63 mmol) followed by azobisisobutyronitrile (0.054 g, 0.33 mmol). The reaction mixture was heated at 75 C for 18 h. The reaction mixture was diluted with dichloromethane, washed with water, dried over anhydrous sodium sulfate, filtered and concentrated. The crude was purified by silica gel column chromatography, using 50% ethyl acetate in hexane to afford methyl 6- (bromomethyl)nicotinate (0.28 g, 37% yield) as a brownish solid. Calculated M+H: 229.97; Found M+H: 230.01.

Statistics shows that 5470-70-2 is playing an increasingly important role. we look forward to future research findings about Methyl 6-methylnicotinate.

Reference:
Patent; MNEMOSYNE PHARMACEUTICALS, INC.; ANDERSON, David R.; VOLKMANN, Robert A.; WO2015/48503; (2015); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1335210-23-5, 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 1335210-23-5 as follows.

Examples 9 and 10 Preparation of Compounds 9 and 1Theta (2S,5R,13aS)-N-((R)-H4-fluoroph^ octahydro-2,5-methanopyrido[ 1 ‘,2′:4,5]pyrazino[2, 1 -b][ 1 ,3]oxazepine- 10-carboxamide 9 and (2R,5S,13aR)-N-((R)-l-(4-fj.uorophenyl)ethyl)-8-hydroxy-7,9-dioxo- 2,3,4,5 J,9,13,13a-octahydro-2,5-methanopyrido[r,2’:4,5]pyrazino[2, b] [ 1 ,3]oxazepine- 10-carboxamide 10 Step 1 l-(2,2-dimethoxyethyl)-5-methoxy-6-(methoxycarbonyl)-4-oxo-l ,4- dihydropyridine-3-carboxylic acid (1-A, 0.500 g, 1.59 mmol), was suspended in acetomtrile (6 rnL) and treated with N,N-diisopropylethylamine (DIPEA) (0.550 mL, 3.17 nifflol), (R)-l-(4-fluoropbenyi)ethanamine (0.242 rng, 1.74 mmol) and HATXJ (0.661 g, 1.74 mmol). The reaction mixture was stirred for 2 hours and partitioned between ethyl acetate and water. The organic layer was separated and washed with HCl ( 10% aq), sodium bicarbonate (1 M aq), dried over sodium sulfate, filtered and concentrated to afford crude (R)-methyl l -(2,2-dimethoxyethyl)-5-(l -(4- fiuorophenyl)ethylcarbamoyl)-3-methoxy-4-oxo-l ,4-dihydropyridine-2-carboxylate which was used without purification in the next step: LCMS-ESI+ (m/z): [M+H] ; calculated for C”.< ; i ^ X -()··: 437.17; found: 437.1. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1335210-23-5, its application will become more common. Reference:
Patent; GILEAD SCIENCES, INC.; JIN, Haolun; LAZERWITH, Scott, E.; MARTIN, Teresa, Alejandra, Trejo; BACON, Elizabeth, M.; COTTELL, Jeromy, J.; CAI, Zhenhong, R.; PYUN, Hyung-Jung; MORGANELLI, Philip, Anthony; JI, Mingzhe; TAYLOR, James, G.; CHEN, Xiaowu; MISH, Michael, R.; DESAI, Manoj, C.; WO2014/100323; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem