Tag: M.W=300-400

Electric Literature of 96428-50-1 , The common heterocyclic compound, 96428-50-1, name is Ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate, molecular formula is C18H18N2O3, 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.

Example 24A Ethyl 8-hydroxy-2-methylimidazo[1,2-a]pyridine-3-carboxylate 31.45 g (101.3 mmol) of ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate from Example 23A were dissolved in 2 l of ethyl acetate, 3.15 g of 10% Pd/carbon were added and the mixture was stirred at RT and standard hydrogen pressure for 5 h. The mixture was filtered through kieselguhr, the filter cake was washed well with ethyl acetate/methanol and the filtrate was concentrated to dryness. This gave 21.94 g of the target compound (98% of theory, purity 99%). LC-MS (Method 1): Rt=0.61 min MS (ESpos): m/z=221 (M+H)+ 1H-NMR (400 MHz, DMSO-d6): delta=1.36 (t, 3H), 2.60 (s, 3H), 4.36 (q, 2H), 6.78 (d, 1H), 6.98 (t, 1H), 8.73 (d, 1H), 10.60 (br s, 1H).

The synthetic route of 96428-50-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; VAKALOPOULOS, Alexandros; VALOT, Gaelle; LINDNER, Niels; FOLLMANN, Markus; WUNDER, Frank; STASCH, Johannes-Peter; MARQUARDT, Tobias; REDLICH, Gorden; DIETZ, Lisa; Ll, Volkhart Min-Jian; (94 pag.)US2017/57954; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1053656-51-1, Ethyl 5-Boc-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate, 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, Computed Properties of C14H20N2O4S, blongs to pyridine-derivatives compound. Computed Properties of C14H20N2O4S

[00253] 1C. (Z)-Ethyl 5-( ,N’-bis(tert-butoxycarbonyl)carbamimidoyl)-4,5,6,7- tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate: 5-tert-Butyl 2-ethyl 6,7- dihydrothiazolo[5,4-c]pyridine-2,5(4H)-dicarboxylate (0.500 g, 1.601 mmol) was treated with HC1 (4.0M in dioxane) (20.01 ml, 80 mmol) at room temperature. After 1 h, the precipitate was filtered, washed with Et20, and dried in vacuo. The amine hydrochloride salt was dissolved in DMF (10 mL) and treated with DIPEA (1.677 ml, 9.60 mmol) and (E)-tert-butyl (((tert-butoxycarbonyl)amino)( lH-pyrazol- 1 -yl)methylene)carbamate (0.497 g, 1.601 mmol). After 14 h, the reaction mixture was taken up in EtOAc (50 mL) and washed with water. The water layer was extracted with additional EtOAc. The combined organic layers were washed with 1.0M HQ solution, water, brine, dried over sodium sulfate, filtered, and concentrated. The crude material was purified by column chromatography to give 1C (0.282 g, 38.8 % yield) as a white solid. MS (ESI) m/z: 455 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1053656-51-1, Ethyl 5-Boc-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.P.; CLARK, Charles G.; ORWAT, Michael J.; SMITH II, Leon M.; EWING, William R.; WO2014/59202; (2014); 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. 59020-10-9, name is 3-(Tributylstannyl)pyridine, molecular formula is C17H31NSn, 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. COA of Formula: C17H31NSn

General procedure: Aryl halide (0.5 mmol), base (1 mmol), CuI (20 mol %), alkylstannylpyridine(0.75 mmol), and catalyst (1 mol %) were dissolvedin DMF (2 mL) in a 10 mL vial and heated at a specific temperatureunder N2 for 12 h. After the reaction was complete, and thenquenched with water. The mixture was diluted with ethyl acetate(10 mL), filtered through a pad of Celite, and followed by extractionwith ethyl acetate for three times. The combined organic layer wasdried over anhydrous Na2SO4, filtered, and evaporated under reducedpressure. The residual was purified by flash chromatographyon silica gel (ethyl acetate/hexane) to give the desired product.4.3.5 3-(4-Methoxyphenyl)pyridine (3ea) 14 Yellow solid, mp 57-58 C; 1H NMR (400 MHz, CDCl3): delta=8.82 (s, 1H), 8.54 (d, J=4.08 Hz, 1H), 7.83 (dt, J=7.88, 1.88 Hz, 1H), 7.52 (d, J=8.72 Hz, 2H), 7.32-7.35 (m, 1H), 7.01 (d, J=8.72 Hz, 2H), 3.86 (s, 3H); 13C NMR (100 MHz, CDCl3): delta=55.4, 114.5, 123.5, 128.2, 130.2, 133.9, 147.9, 148.0, 159.7; HRMS-ESI (m/z): [M+H]+ calcd for C12H12NO+: 186.0913, found: 186.0915.

With the rapid development of chemical substances, we look forward to future research findings about 59020-10-9.

Reference:
Article; Ma, Gaizhi; Leng, Yuting; Wu, Yusheng; Wu, Yangjie; Tetrahedron; vol. 69; 2; (2013); p. 902 – 909;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 578007-66-6 , The common heterocyclic compound, 578007-66-6, name is 5-Bromo-3-iodo-2-methoxypyridine, molecular formula is C6H5BrINO, 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.

Step 1: tert-Butyl (1-(4-((5-bromo-2-methoxypyridin-3- yl)ethynyl)phenyl)cyclobutyl)carbamate: To a degassed solution of 5-bromo-3-iodo-2- methoxypyridine (823 mg, 2.62 mmol) in triethylamine (8.0 mL) at 0 C was added Pd(PfBu3)2 (1 10.4 mg, 6 mol%), Cul (5.0 mg, 1 mol%) and terf-butyl (1-(4- ethynylphenyl)cyclobutyl)carbamate (71 1 mg, 2.62 mmol). The brown suspension was stirred for 56 hours at room temperature before the reaction mixture was suspended in dichloromethane and washed with brine, dried over magnesium sulphate, filtered and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (gradient 10 to 25% EtOAc in hexane) to give the title compound as a white solid (1.04 g, 87%). H-NMR (500 MHz, CDCI3) delta 8.14 (d, 1 H), 7.84 (d, 1 H), 7.52 (dd, 2H), 7.41 (d, 2H), 5.13 (bs, 1 H), 4.01 (s, 3H), 2.50-2.56 (m, 4H), 2.09-2.14 (m, 1 H), 1.84-1.90 (m, 1 H), 1.36 (bs, 9H).

The synthetic route of 578007-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMAC DISCOVERY LIMITED; BELL, Mark, Peter; O’DOWD, Colin, Roderick; ROUNTREE, James, Samuel, Shane; TREVITT, Graham, Peter; HARRISON, Timothy; MCFARLAND, Mary, Melissa; WO2011/55115; (2011); 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. 53710-18-2, name is 3,5-Diiodopyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H3I2N

To a mixture of 4-(3-butenyloxy)-2,6-diethynylpyridine (4, 0.10 g, 0.51 mmol), 3,5-diiodopyridine (6, 0.63 g, 2.0 mmol), Pd(PPh3)4 (24 mg,21 mol), i-Pr2NH (2.5 mL), and THF (20 mL) was added CuI (3.9 mg, 20 mol), and the mixture wasstirred for 5 h at room temperature. The resulting mixture was treated with a Florisil bed and given a rinsewith AcOEt. The filtrate was concentrated by a rotary evaporator and the resulting residue was subjectedto silica gel column chromatography (eluent: CHCl3 to CHCl3/MeOH = 50:1) to give 7 as a colorless solid(0.16 g, 52%). Mp 196-198 C; IR (KBr) 3047, 2925, 2222, 1582, 1550 cm-1; 1H NMR (CDCl3) 2.57-2.64 (m, 2 H), 4.13 (t, J = 6.6 Hz, 2 H), 5.15-5.23 (m, 2 H), 5.82-5.95 (m, 1 H), 7.07 (s, 2 H), 8.21 (s,2 H), 8.73 (s, 2 H), 8.81 (s, 2 H); 13C NMR (CDCl3) 33.2, 67.8, 84.0, 92.1, 92.4, 113.9, 117.9, 120.8, 133.1,143.8, 146.6, 150.7, 155.2, 165.1; HRMS (ESI-TOF) calcd for C23H16I2N3O (M + H+): 603.9383; m/zfound: 603.9362.

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, 53710-18-2, 3,5-Diiodopyridine.

Reference:
Article; Abe, Hajime; Suzuki, Daiki; Shimizu, Ayako; Inouye, Masahiko; Heterocycles; vol. 88; 1; (2014); p. 547 – 557;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 123853-39-4 ,Some common heterocyclic compound, 123853-39-4, molecular formula is C16H15Cl2NO4, 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.

Step 1 preparation of intermediate 2.0 kg (5.61mol) inputs 10L in acetonitrile, inputs under stirring chloro-butyrate 850g (6.22mol) and potassium carbonate 860g (6.22mol), heating to reflux reaction 4-6h, cooling to room temperature, filter, filtrates in 40-50 C concentrated under reduced pressure to dry, subsequently joined 4L ethyl acetate, reflux is dissolved, and 45g activated carbon decolourizations 5-15min, hot filtering, filtrates in 30-40 C dropwise 7L-hexane crystallization, filtration, 40-50 C decompression drying to obtain the butyric acid clevidipine 2.38 kg, yield 92.89%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,123853-39-4, its application will become more common.

Reference:
Patent; Hefei long promise Pharmaceutical Technology Co; Wu, biao; Ling, lin; Wang, zhouhong; Dai, yij; (10 pag.)CN105461619; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 79491-46-6, 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 79491-46-6, name is 2,6-Dibromo-3-methoxy-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Alternate Procedures Useful for the Synthesis of Compound 39 Preparation of 5,7-dibromo-4-methoxy-7-azaindole 36: Vinylmagnesium bromide (0.85 M in THF, 97.7 mL, 83.0 mmol) was added over 30 min. to a stirring solution of 2,6-dibromo-3-methoxy-5-nitropyridine (7.4 g, 23.7 mmol) in THF (160 mL) at -75 C. The solution was stirred 1 h at -75 C., overnight at -20 C., recooled to -75 C. and quenched with saturated aqueous NH4Cl (~100 mL). The reaction mixture was allowed to warm to rt, washed with brine (~100 mL) and extracted with Et2O (150 mL) and CH2Cl2 (2*100 mL). The combined organics were dried (MgSO4), filtered and concentrated. The residue was purified by flash column chromatography (SiO2, 3:1 hexanes/EtOAc) to yield 5,7-dibromo-4-methoxy-7-azaindole 36 (1.10 g, 3.60 mmol, 15%) as a pale yellow solid.

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 79491-46-6, 2,6-Dibromo-3-methoxy-5-nitropyridine.

Reference:
Patent; Wang, Tao; Wallace, Owen B.; Zhang, Zhongxing; Meanwell, Nicholas A.; Bender, John A.; US2002/119982; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 928653-73-0, 5-Bromo-2-chloro-3-iodopyridine, 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, SDS of cas: 928653-73-0, blongs to pyridine-derivatives compound. SDS of cas: 928653-73-0

To a reaction vessel (lO0mL) in a nitrogen environment containing 3 (5g, I 5.7mmol) were added trans-phenylvinylboronic acid 4 (2.7g, 1 8mmol), tetrakis triphenylphosphine (907mg, 0.8mmol), sodium carbonate (4.2g, 39mmol) in 1 ,4-dioxane(1 OOmL). The mixture was stirred at refiux for 24 hours until consumption of starting material followed by TLC. The product was cooled to room temperature; it was filtered on celite. The solution was dried on MgSO4, filtered and evaporated. The residue was purified by chromatography (c-hexane:ethyl acetate99: 1, then 98:2) to afford 5-bromo-2-chloro-3- ((E)-styryl)pyridine 5 (yield: 93%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,928653-73-0, 5-Bromo-2-chloro-3-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; CENTRE REGIONAL DE LUTTE CONTRE LE CANCER FRANCOIS BACLESSE; UNIVERSITE DE CAEN BASSE-NORMANDIE; INSTITUT DE CANCEROLOGIE DE L’OUEST RENE GAUDUCHEAU; POULAIN, Laurent; VOISIN-CHIRET, Anne-Sophie; SOPKOVA-DE OLIVEIRA SANTOS, Jana; BUREAU, Ronan; BURZICKI, Gregory; DE GIORGI, Marcella; PERATO, Serge; FOGHA, Jade; RAULT, Sylvain; JUIN, Philippe; GAUTIER, Fabien; WO2015/132727; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 193274-02-1, name is tert-Butyl 3a-benzyl-2-methyl-3-oxo-3a,4,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-5(3H)-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C19H25N3O3

Step D. 3a(R)-Benzyl-2-methyl-2,3,3a,4,6,7-hexahydro-pyrazolo[4,3-c]pyridin-3-one (L)-tartrate . To a 2 liter, round bottom flask, equipped with a mechanical stirrer, addition funnel, and a thermocouple was added, sequentially, 3a-(R,S)-benzyl-2-methyl-3-oxo-2,3,3a,4,6,7-hexahydro-pyrazolo[4,3-c]-pyridine-5-carboxylic acid tert-butyl ester (prepared according to Step C, 51.5g, 0.15 moles, 1.0 equivalents) and methylene chloride (515 ml, 10 volumes). The mixture was agitated to form a solution which was then cooled to an internal temperature of 0C-5C. To the cooled mixture was added trifluoroacetic acid (TFA, 130ml, 192g, 1.68 moles, 11.2 eq., 2.5 volumes). The TFA was added via the addition funnel over 15 minutes while maintaining an internal temperature of 0C-5C. The reaction mixture was warmed to about 20C over 3 hours and then the reaction mixture was cooled to 10C-15 C. To the cooled reaction mixture was added sodium carbonate (92g, 0.868 moles) in water (920 mL) over 20 minutes. The pH was 7.5. The reaction mixture was transferred to a 2 liter separatory funnel and allowed to settle. The organic portion was decanted and the aqueous portion was extracted with methylene chloride (130ml, 2.5 volumes). The combined organic portions were transferred back to the 2 liter reactor and to it was added L-tartaric acid (24.77g, 0.165 moles, 1.1 equivalents) dissolved in acetone (354 ml, about 7 volumes) and water (44mL, about 1 volume). The reaction mixture was agitated and heated at about 38C overnight. The resultant slurry was cooled to 0C-5C, granulated for 1 hour, then filtered. The solids were washed with 100ml of cold acetone and then dried in vacuoat 40C-50C for 16 hours to afford 51.86g (87.9% yield) of the title compound of Step D.

With the rapid development of chemical substances, we look forward to future research findings about 193274-02-1.

Reference:
Patent; Pfizer Products Inc.; EP1031575; (2000); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 153747-97-8, tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, 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, Product Details of 153747-97-8, blongs to pyridine-derivatives compound. Product Details of 153747-97-8

To a solution of 4-(5-bromo-pyridin-2-yl)-piperazine-l-carboxylic acid tert-butyl ester (250 mg, 0.73 mmol) in 3.5 mL anhydrous THF was added 1.6 M /j-butyllithium (500 muL, 0.80 mmol) at -78 0C under nitrogen atmosphere. After stirring for 45 min, the reaction mixture was charged with oxetan-3-one (131 mg, 1.82 mmol) in 200 muL DCM. The reaction mixture was stirred at -78 0C for 2 h and at room temperature for 16 h. The mixture was quenched with saturated ammonium chloride aqueous solution and the mixture was partitioned between DCM and brine. The organic layer was dried over Na2SO4 and concentrated to afford the crude material. The resulting solid was purified by flash chromatography on silica gel, eluting with 20 – 100% EtOAc: heptane. Fractions containing the desired product were combined and concentrated to afford a off white solid (80 mg, 32.7% yield). The Boc protected title compound (140 mg, 0.417 mmol) was dissolved in DCM and charged with lutidine (194 muL, 1.67 mmol). The reaction mixture was cooled at 0 0C, charged with trimethylsilyl trifluoromethanesulfonate (1.25 mmol, 228 uL) and stirred at 0 0C for 2 h. The reaction mixture was poured into ice and the mixture was partitioned between DCM and water. The organic layer was dried over Na2SO4 and concentrated to afford a brown greasy solid (70 mg, yield 71%). MS (m/z, MH+): meas. 236.4 calc. 236.3

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153747-97-8, tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; WO2008/110611; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem