Tag: M.W:200-300

Electric Literature of 162102-79-6, Adding some certain compound to certain chemical reactions, such as: 162102-79-6, name is Dimethyl 4-bromopyridine-2,6-dicarboxylate,molecular formula is C9H8BrNO4, 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 162102-79-6.

[60] In a sealed tube, a mixture of 1 [61] (2.74 g,10 mmol) and (R or S)-phenylglycinol (3.43 g, 25 mmol) in methanol (10 mL) was stirred at 115 C for 12 h. After cooling toroom temperature, the crude product was poured into ice water(100 mL), stirred for 15 min, filtered, washed with water(20 mL 3) and the residues was dried under vacuum. The whiteproduct was used for the next step without further purification (4.41 g, 91%). 1H NMR (400 MHz, CDCl3): d 8.60 (d, J 7.6 Hz, 2 H),8.45 (s, 2 H), 7.37-7.29 (m, 10 H), 5.26-5.22 (m, 2 H), 4.01 (d,J 4.4 Hz, 4 H), 2.21 (br, 2 H).

According to the analysis of related databases, 162102-79-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Ya-Qi; Pan, Yao; Gao, Wan-Qing; Wu, Yuan; Liu, Chun-Hua; Zhu, Yuan-Yuan; Tetrahedron; vol. 75; 28; (2019); p. 3809 – 3814;,
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Reference of 89284-11-7, 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. 89284-11-7, name is 5,6-Dibromopyridin-2-amine, molecular formula is C5H4Br2N2, 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 mixture of 5,6-dibromopyridin-2-amine (80 g, 318 mmol), ethynylbenzene (78 ml, 698 mmol), copper(I) iodide (1.51 g, 7.94 mmol), Dichlorobis(triphenylphosphine)- palladium(II) (5.79 g, 7.94 mmol) and triethylamine (110 ml, 794 mmol) is stirred under argon atmosphere in ACN (500 ml) with THF (250 ml) for 21 h at 50C. The mixture is diluted with water and extracted with DCM. The combined organic layers are dried over MgS04, concentrated in vacuo and the product purified by NP chromatography. Yield: 82 g (94%). HPLC-MS: M+H=273/275; tR=1.34 min (*Method_l).

According to the analysis of related databases, 89284-11-7, the application of this compound in the production field has become more and more popular.

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

Electric Literature of 884494-81-9, 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.884494-81-9, name is 3-Bromo-5-fluoro-2-methoxypyridine, molecular formula is C6H5BrFNO, molecular weight is 206.01, as common compound, the synthetic route is as follows.

PREPARATION 10; (5-Fluoro-2-methoxypyridin-3-yl)boronic acid n-Butyllithium (1.6 M solution in hexanes, 20 mL, 32 mmol) was slowly added (0.4 mL/min) to a solution of 3-bromo-5-fluoro-2-methoxypyridine (6.0 g, 29.12 mmol) and triisopropylborate (8.4 mL, 36.62 mmol) in dry tetrahydrofuran (70 mL) at -100 C under argon atmosphere. The reaction mixture was stirred at -100 C for 2 hours and afterwards the temperature was allowed to warm up slowly overnight to ambient temperature before being cooled down to 0 C. Aqueous hydrochloric acid (1 N solution, 120 mL) was slowly added and the mixture was stirred at 0 C for 1 hour. A solution of sodium hydroxide (32% in water) was then added until pH was around 6 and the resulting mixture was extracted with diethyl ether (chi3). The combined organic layers were dried over magnesium sulphate and the solvent removed under reduced pressure to yield the title compound (3.28 g, 66%) as a white solid. X LRMS (m/z): 172 (M+1)+.1H-NMR delta (300 MHz, CDCI3): 4.04 (s, 3H), 6.00 (s, 2H), 7.88 (dd, 1 H), 8.09 (d,1 H).

The chemical industry reduces the impact on the environment during synthesis 884494-81-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ALMIRALL,S.A.; GONZALEZ RODRIGUEZ, Jacob; VIDAL JUAN, Bernat; VIDAL GISPERT, Laura; BACH TANA Jordi; WO2012/69202; (2012); A1;,
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Related Products of 10235-65-1 ,Some common heterocyclic compound, 10235-65-1, molecular formula is C9H5Cl2N3, 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.

Sodium Hydride (31 .8 mg, 0.796 mmol) was added to DMF (1 mL), followed by 3,4-dihydro-1 (2H)- isoquinolinone (107 mg, 0.730 mmol). The resulting suspension was stirred at r.t. for 5 min, then 4,6- dichloro-2-(2-pyridinyl)pyrimidine (150 mg, 0.664 mmol) was added and resulting mixture was stirred at r.t. for 45 min.The mixture was partitioned between EtOAc and water then the aqueous layer extracted with DCM three times. The organic layers were combined, filtered throught a phase separator and volatiles removed under reduced pressure to afford 212 mg of a white-brown powder.The crude material was purified by column chromatography, eluting with a 0 to 100% EtOAc in cyclohexane, to give the title compound, 121 mg (54%) as an off white powder.LCMS (Method A) Rt 1 .05 min, MH+=337.0

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. 10235-65-1, 4,6-Dichloro-2-(pyridin-2-yl)pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; ATKINSON, Stephen John; BARKER, Michael David; CAMPBELL, Matthew; HUMPHREYS, Philip; LIDDLE, John; SHEPPARD, Robert John; WILSON, David; WO2012/52390; (2012); A1;,
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Pyridine | C5H5N – PubChem

Application of 159503-91-0, 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 159503-91-0, name is tert-Butyl 4-bromo-5,6-dihydropyridine-1(2H)-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

2nd step: under the protection of nitrogen, the 1M isopropyl magnesium chloride-lithium chloride (88 ml, 88mmol) into the reaction bottle, temperature control -15 C to -5 C, dropwise N-Boc-1, 2, 5, 6-tetrahydro-pyridine-4-bromo, 2-methyl tetrahydrofuran (90 ml) solution, stirring finishing joining 1-2 hours. After the end of the exchange, then drop by adding isopropoxy boric acid pinacone ester (16.4g, 88mmol), subsequently maintain the reaction at room temperature overnight. Adding 10% hydrochloric acid aqueous solution quenching reaction, adjusting PH= 4-5, by adding 160 ml ethyl acetate, saturated salt water an organic layer, the organic layer after evaporation to dryness, add ethanol/heptane 5:1 obtained after pulping 18.9g N-Boc-1 needle-like white crystals, 2, 5, 6-tetrahydro-pyridine-4-boronic acid frequency that alcohol ester, GC: 99.6%, yield: 61%.

According to the analysis of related databases, 159503-91-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cangzhou Purui Oriental Technology Co., Ltd; Leng, Yanguo; Zhang, Shihong; Liu, Jinzou; (6 pag.)CN105566367; (2016); A;,
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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. 1001413-01-9, name is 1-(3,4-Difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C13H9F2NO3

The carboxylic derivative 3 (300 mg, 1.13 mmcl) and the amine 2(168 mg, 1.13 mmcl) were combined through a condensation reaction in presence of thecondensing agent TBTU (363 mg, 1.13 mmol). The solvents were evaporated under reduced pressure and the crude product was purified by flash chromatography over silica gel, using 0 – 4% MeOH as a gradient in CHCI3, to obtain pure SST143 as a white solid (210 mg, 0.53 mmol, 47% yield). mp: 285-288 00 1H-NMR (400 MHz, DMSO-d6): 6 3.48 (5, 2H, CH2 indole); 5.28(5, 2H, CH2); 6.68 (dd, 1 H, J= 6.8, 7.2 Hz, Ar); 6.77 (d, 1 H, J= 8.4 Hz, Ar); 7.20-7.23 (m, 1H, Ar); 7.40-7.52 (m, 3H, Ar); 7.66 (5, 1H, Ar); 8.29 (dd, 1H, J= 2.2,6.8 Hz, Ar); 8.46 (dd, 1H, J= 2.2, 6.8 Hz, Ar); 10.33 (5, 1H, NH), 11.87 (5, 1H,NH) ppm. 13C-NMR (101 MHz, DMSO-d6): 6 176.23, 161.54, 160.73, 150.35,147.90, 143.78, 143.42, 139.86, 134.02, 132.32, 126.40, 124.90, 120.35,119.02, 117.74, 117.25, 116.90, 109.10, 107.22, 51.45, 36.02 ppm. 19F-NMR (376 MHz; DMSO-d6): 6-138.17 (d, iF, J= 24 Hz); -139.76 (d, iF, J= 24 Hz) ppm. Anal. Calcd for 021H15F2N303: 0, 63.80%; H, 3.82%; N 10.63%; Found: C, 63.72%; H, 3.55%; N, 10.50%

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, 1001413-01-9, 1-(3,4-Difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid.

Reference:
Patent; INTERNATIONAL SOCIETY FOR DRUG DEVELOPMENT S.R.L.; SESTITO, Simona; DANIELE, Simona; MARTINI, Claudia; RAPPOSELLI, Simona; PURICELLI, Guido; (63 pag.)WO2016/198597; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 102368-13-8 ,Some common heterocyclic compound, 102368-13-8, molecular formula is C11H8N2O2S, 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 mixture of N-(3-amino-2,4-difluoro-benzyl)-2,2-dimethyl-propionamide (570 mg, 2.35 mmol), 1,1′-thiocarbonyldi-2(1H)-pyridone (550 mg, 2.35 mmol) and dioxane (20 mL) is stirred at reflux overnight. The reaction mixture is concentrated, diluted with DCM, filtered through a pad of silica gel and the filtrate is concentrated to give the title compound.Yield: 440 mg (65%). Rf=0.80 (silica gel, DCM:EtOH 95:5).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,102368-13-8, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/149676; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 945557-04-0, 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.945557-04-0, name is 5-Bromo-3-chloropicolinonitrile, molecular formula is C6H2BrClN2, molecular weight is 217.4505, as common compound, the synthetic route is as follows.

Acetyl 2,4,6-tri-O-acetyl-3 -azido-3 -deoxy- 1 -thio-cL-D-galactopyranoside (250 mg, 0.64 mmol) and 5-bromo-3-chloro-pyridine-2-carbonitrile (280 mg, 1.28 mmol) were dissolved in DMF (10 mL). Diethylamine (0.15 ml) was added. The reaction was stirred at room temperature with for 20 h. Water (50 mL) and DCM (50 mL) were added. The aqueous phase was extracted with DCM (50 mL X 2), the combined organic phases were washed with water (100 mL) and brine (100 mL), dried over anhydrous sodium sulphate. Removal of solvent gave a residue. The residue was purified by column chromatography (PE/EA=3/1) to obtain the product (130 mg, 38%).5-Chloro-6-cyano-3-pyridyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-cL-D- galactopyranosidein/z calcd for [C18H18CLN5O7S] [M+H]: 484.0; found: 484.0.5-Bromo-2-cyano-3-pyridyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-cL-D- galactopyranosidein/z calcd for [C18H18BrN5O7S] [M+H]: 528.0; found: 528.0. To a mixture of 5-Chloro-6-cyano-3-pyridyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1- thio-cL-D-galactopyranoside and 5 -Bromo-2-cyano-3 -pyridyl 2,4,6-tri-O-acetyl-3 – azido-3-deoxy-1-thio-cL-D-galactopyranoside (130 mg) in CH3CN (5 mL) were added DIEA (0.23 mL), Copper(I)Iodide(15 mg, 0.08 mmol), CsF(82 mg, 0.54 mmol), 2-(4- chloro-3 ,5 -difluoro-phenyl)ethynyl-trimethyl-silane( 132 mg, 0.54 mmo 1). The reaction was stirred at room temperature for 20 h under a N2 atmosphere. Water (10 mL) and DCM (10 mL) were added. The aqueous phase was extracted with DCM (5 mL X 2), the combined organic phases were washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulphate. Removal of solvent gave a residue. The residue was purified by column chromatography (PE/EA=2/1) to obtain the products 110 (80mg) and 111 (20mg).110) 5-Chloro-6-cyano-3-pyridyl 2,4,6-tri-O-acetyl-3-deoxy-3- [4-(4-chloro-3,5- difluorophenyl)- 1H- 1 ,2,3-triazol- l-ylj – 1-thio-a-D-galactopyranosidem/z calcd for [C26H21Cl2F2N5O7S] [M+H]: 656.0; found: 656.0.1H NMR (400 MHz, CDC13) oe 8.63 (d, J 1.9 Hz, 1H), 8.01 (d, J 2.0 Hz, 1H), 7.83 (s, 1H), 7.45 (t, J= 6.3 Hz, 2H), 6.34 (d, J 5.5 Hz, 1H), 6.16 (dd, J 11.7, 5.6 Hz, 1H), 5.63 (d,J= 2.3 Hz, 1H), 5.20 (dd,J= 11.7, 3.1 Hz, 1H), 4.78 -4.71 (m, 1H), 4.14 (tdd, J= 12.8, 8.7, 4.4 Hz, 3H), 2.08 (s, 3H), 2.00 (s, 3H), 1.98 (s, 3H).ill) 5-Bromo-2-cyano-3-pyridyl 2,4,6-tri-O-acetyl-3-deoxy-3- [4-(4-chloro-3,5- difluorophenyl)- 1H- 1 ,2,3-triazol- l-ylj – 1-thio-cL-D-galactopyranosidem/z calcd for [C26H2iBrCIF2N5O7S] [M+H]: 700.0; found: 700.0.

Statistics shows that 945557-04-0 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-3-chloropicolinonitrile.

Reference:
Patent; GALECTO BIOTECH AB; ZETTERBERG, Fredrik; NILSSON, Ulf; LEFFLER, Hakon; (105 pag.)WO2018/11094; (2018); 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. 38940-62-4, name is 3-Acetyl-5-bromopyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 3-Acetyl-5-bromopyridine

A solution of 1-(5-bromopyridin-3-yl)ethanone (2.04 g, 27.5 mmol) in methanol (55 mL) was added slowly to a cold solution of 2-oxoacetic acid (2.04 g, 27.5 mmol) and potassium carbonate (7.22 g, 52.24 mmol) in water (50 mL). The mixture was stirred at room temperature for 2h. The resultant solution was partially evaporated under reduced pressure at 30 C to remove most of the methanol and then extracted three times with ethyl acetate. The cooled aqueous solution was carefully treated with acetic acid (11 mL, 192 mmol) and washed with dichloromethane. Ethylhydrazine oxalate (3.61 g, 26.1 mmol) was added to the aqueous phase, and the mixture heated under reflux for 2 h. A further 3.61 g ethylhydrazine oxalate (26.12mmols) was added and the mixture heated under reflux for 2 d. The solution was neutralised with potassium carbonate to pH 7 and was extracted three times with ethyl acetate. The combined organic layers were washed with brine, and dried over anhydrous sodium sulphate. The solvent was removed under reduced pressure and the crude purified in a 40M column from Biotage on a SP1 automatic purification system using hexane and ethyl acetate as solvents (0-100% ethyl acetate) in 20 column volumes. The appropriate fractions were collected and evaporated to give 3.71 g (47% yield) of the title compound. HPLC/MS (9 min) retention time 5.32 min. LRMS: m/z 282 (M+1)

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, 38940-62-4, 3-Acetyl-5-bromopyridine.

Reference:
Patent; Almirall, S.A.; EP2196465; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 65001-21-0, 5-Bromopyridine-3-sulfonyl chloride, 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, 65001-21-0, blongs to pyridine-derivatives compound. Safety of 5-Bromopyridine-3-sulfonyl chloride

Crude 5 -bromopyridine-3-sulfonyl chloride from step 1 above was dissolved in THF (14 L, 8 vol) and then transferred to a 20 L RB flask equipped with mechanical stirrer under inert atmosphere. The solution was cooled to 0-5C and tert- butyl amine (1.95 Kg, 26.66 moles) was added at 0-5C. Upon completion of addition, the reaction mixture was warmed to ambient temperature where it stirred for 2 h. At the conclusion of this period, the reaction progress was monitored by HPLC, which indicated that the reaction was complete. The solvent was evaporated under vacuum to give a thick residue. The residue was dissolved in ethyl acetate (18 L, 12 vol). The organic layer was separated, washed with water (9 L, 5 vol) and then concentrated under vacuum to yield a residue. Hexanes (9 L, 5 vol) were added to the residue and the product precipitated out and was collected by filtration to yield a free flowing yellow solid (1.5 Kg, 54.28% overall yield). ¾ NMR (DMSO-D6, 400 MHz, delta ppm); 8.99 (d, J = 2Hz, 1H), 8.81 (d, J= 2 Hz, 1H), 8.29 (t, J= 2Hz, 1H). [M++l] = 293.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,65001-21-0, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; JOHNSON, James A.; LLOYD, John; FINLAY, Heather; JIANG, Ji; NEELS, James; DHONDI, Naveen Kumar; GUNAGA, Prashantha; BANERJEE, Abhisek; ADISECHAN, Ashokkumar; WO2011/28741; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem