Tag: M.W:200-300

Synthetic Route of 717843-56-6, 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. 717843-56-6, name is 3-Bromo-2-methoxy-5-methylpyridine, molecular formula is C7H8BrNO, 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 AM2: 3-Bromo-5-bromomethyl-2-methoxy-pyridine To a solution of 3-bromo-2-methoxy-5-methyl-pyridine (Step AM3) (3.0 g, 14.7 mmol), was added NBS (3.1 g, 17.6 mmol) and AIBN (121 mg, 0.7 mmol) and the mixture was stirred at 80 C. for 1 h. H2O and CH2Cl2 were added and the phases were separated. The organic layer was dried (MgSO4), filtered and concentrated. The crude product was purified by silica gel column chromatography (heptane/EtOAc, 95:5?0:100). tR: 1.10 min (LC-MS 1).

According to the analysis of related databases, 717843-56-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; Cotesta, Simona; Furet, Pascal; Guagnano, Vito; Holzer, Philipp; Kallen, Joerg; Mah, Robert; Masuya, Keiichi; Schlapbach, Achim; Stutz, Stefan; Vaupel, Andrea; US2013/317024; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 137778-20-2, 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 137778-20-2, name is 5-Bromo-6-methylpicolinic acid. This compound has unique chemical properties. The synthetic route is as follows.

Example 10Methyl 5-bromo-6-methyl-2-pyridine carbonate synthesisInto a 500-l. glass-lined reactor was placed 5-bromo-6-methyl-2-pyridine carboxylic acid (30 kg, 138.9 moles) and methanol (133 kg, 4156 moles). The mixture was agitated and thionyl chloride (36.8 kg, 309.2 moles) was added while the temperature was maintained between 2030 C. After the addition, the mixture was heated to 5565 C. for 2 hrs. The reaction was stopped when the raw material was detected at less than 2%. Then solvent was removed by concentration at a temperature below 40 C. MTBE (280 kg) was added and the mixture was stirred for another 30 min. to dissolve the crude. Then the MTBE solution was transferred to one drum. To the above reactor was added water (300 kg). Then the solution containing the crude was pumped to the reactor while maintaining the reactor contents at 05 C. and stirred for 1 hr. After phase separation, the aqueous layer was extracted with MTBE (60 kg). The organic phases were combined, and concentrated at a temperature below 40 C. Hexane (60 kg) was added to the residue. The obtained solid was stirred, centrifuged and dried. White powder (22.36 kg, 97.2 moles) was obtained. The purity of the product was >98%, and the mole yield was 70%.

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 137778-20-2, 5-Bromo-6-methylpicolinic acid.

Reference:
Patent; Synergetica Changzhou Chemical Company; US2010/305330; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1235036-15-3 , The common heterocyclic compound, 1235036-15-3, name is tert-Butyl 3-bromo-6-chloropicolinate, molecular formula is C10H11BrClNO2, 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 7A methyl 2-(5-bromo-6-(tert-butoxycarbonyl)pyridin-2-yl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylate A solution of methyl 1,2,3,4-tetrahydroisoquinoline-8-carboxylate (1.00 g), EXAMPLE 1C (1.68 g) and cesium carbonate (2.56 g) was stirred together in N,N-dimethylacetamide (10 mL) at 110 C. overnight. The reaction was cooled, diluted with ethyl acetate (50 mL) and washed with water (2*25 mL) and brine (25 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography using 1-30% ethyl acetate in hexanes provided the title compound.

The synthetic route of 1235036-15-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Inc.; Wang, Le; Doherty, George; Wang, Xilu; Tao, Zhi-Fu; Bruncko, Milan; Kunzer, Aaron R.; Wendt, Michael D.; Song, Xiaohong; Frey, Robin; Hansen, Todd M.; Sullivan, Gerard M.; Judd, Andrew; Souers, Andrew; US2013/96121; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 880870-13-3 ,Some common heterocyclic compound, 880870-13-3, molecular formula is C6H5BrClNO, 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 solution of 5-bromo-2-chloro-4-methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mL) was purged with nitrogen for 15 min. At this point, Zn (CN) 2 (3.96 g, 33.7 mmol) and Pd (Ph3P) 4 (2.60 g, 2.25 mmol) were added, successively. The resulting suspension was stirred at 95 for 12 h under nitrogen atm. The reaction mixture was cooled to ambient temperature, filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue as an oil, which was purified on silica gel and eluted with 0-30 ethyl acetate/hexanes to afford the product. 1H NMR (500 MHz, DMSO-d6) , delta 8.69 (s, 1H) , 7.50 (s, 1H) , 4.04 (s, 3H) LC/MS (M+1) + 169.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,880870-13-3, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; DONG, Shuzhi; GU, Xin; JIANG, Jinlong; SHI, Zhi-Cai; WALSH, Shawn P.; WU, Zhicai; YU, Yang; FERGUSON II, Ronald; GUO, Zhiqiang; FRIE, Jessica; SUZUKI, Takao; BLIZZARD, Timothy A.; FU, Qinghong; VANGELDER, Kelsey F.; (118 pag.)WO2016/65582; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 178876-83-0 , The common heterocyclic compound, 178876-83-0, name is Methyl 6-amino-3-bromopicolinate, molecular formula is C7H7BrN2O2, 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 a solution of methyl 6-amino-3-bromopicolinate (200 mg, 866 umol, 1 eq) in EtOH (50 mL) was added NaHC03 (124 mg, 1.47 mmol, 1.7 eq) and l-chloropropan-2- one (2.35 g, 25.4 mmol, 3.00 mL, 29.3 eq). The reaction was stirred at 90 C for 24 hr. The reaction was cooled to 25 C and concentrated in vacuo. To the residue was added water (50 mL). The aqueous phase was extracted with ethyl acetate (50 mL*3). The combined organic phase was washed with brine (50 mL*2), dried with anhydrous Na2S04, filtered and (0369) concentrated in vacuo. The residue was purified by Prep-TLC (Petroleum ether/Ethyl acetate=l/l). Example 1 14A (120 mg crude) was obtained as a brown oil. ESI m/z 269[M +1 ]+.

The synthetic route of 178876-83-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHRYSALIS, INC.; GWALTNEY, Stephen; (147 pag.)WO2017/214413; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1072438-56-2, 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.1072438-56-2, name is Methyl 6-(aminomethyl)nicotinate hydrochloride, molecular formula is C8H11ClN2O2, molecular weight is 202.6381, as common compound, the synthetic route is as follows.

Preparation 26Methyl 6-[(isobutyrylamino)methvHnicotinateTo an ice-cold suspension of methyl 6-(aminomethyl)nicotinate hydrochloride (1 .00 g, 4.1 8 mmol) and N-ethyl-N-isopropylpropan-2-amine (1 .89 g, 2.55 mL, 14.6 mmol) in DCM (10 mL) was added dropwise a solution of isobutyryl chloride (535 mg, 526 mu, 5.02 mmol) in DCM (3 mL). The reaction mixture was allowed to warm to room temperature, washed with water (5 mL), 1 0% aqueous citric acid solution (5 mL), saturated aqueous sodium bicarbonate solution (5 m L), brine (5 mL), dried over magnesium sulfate, filtered and evaporated to yield the title compound as a pale orange solid (0.988 g, 100%):1H NMR (400 MHz, CDCI3): delta 1 .22 (d, 6H), 2.45 – 2.55 (m, 1 H), 3.95 (s, 3H), 4.62 (d, 2H), 6.67 – 6.68 (br, 1 H), 7.32 – 7.36 (m, 1 H), 8.26 – 8.30 (m, 1 H), 9.15 (s, 1 H).LCMS Rt = 1 .72 minutes MS m/z 237 [MH]+

The chemical industry reduces the impact on the environment during synthesis 1072438-56-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PFIZER LIMITED; BROWN, Alan Daniel; RAWSON, David James; STORER, Robert Ian; SWAIN, Nigel Alan; WO2012/7869; (2012); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 132521-70-1, 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 132521-70-1 as follows.

A suspension of 6-(4-methyl-piperazin-1-yl)-nicotinic acid (200 mg) in DMF (2 ml) was treated under an argon atmosphere with diisopropylamine (0.50 ml), benzylamine (0.12 ml) and BOP (600 mg). The reaction mixture was stirred at r.t. overnight, then diluted with water and extracted with EtOAc. The combined organic layers were washed with water and brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient: CH2Cl2?CH2Cl2/MeOH 9:1) to give N-benzyl-6-(4-methyl-piperazin-1-yl)-nicotinamide (120 mg) as off-white solid. MS (ISP): 311.3 ([M+H]+)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,132521-70-1, its application will become more common.

Reference:
Patent; Galley, Guido; Zbinden, Katrin Groebke; Norcross, Roger; Stalder, Henri; US2009/36452; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 936011-17-5 ,Some common heterocyclic compound, 936011-17-5, molecular formula is C7H6BrNO2, 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 60b (20.5 g, 0.095 mol)was dissolved in THF (400 mL) the resulting solution was stirred at 0C under N2 then treated with LiAlH4 (3.9 g 0.1 mol), maintained the temp below 10C, After addition ,the colorless solution turned to purplish red and stirred at r.t. for 2hrs.TLC showed Compound 232 was consumed, water (4 mL) 15% NaOH (4 mL) and water (12 mL) was added successively the mixture was stirred at r.t for lhr, Na2S04 (50 g) was added, the suspension was filtered off and washed with EA (200 mL), the filtrate was concentrated to give the desired product (Example 60c, 9.4 g, yield 93%) as a brown oil. LCMS [M+H]+=218, 220.

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. 936011-17-5, 5-Bromo-2-methoxyisonicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (212 pag.)WO2017/218960; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 89640-55-1, 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. 89640-55-1, name is 3-Iodo-4-methoxypyridine, molecular formula is C6H6INO, 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 the reaction mixture containing Intermediate IB (31.8 mg, 0.1 mmol) was added 3-iodo-4-methoxypyridine (125.5 mg, 0.534 mmol), sodium carbonate (68.1 mg, 0.643 mmol) and EtOH:DME:H20 (1.2:2.5: 1.0 ratio) (1.5 mL). The reaction mixture was purged with argon, then treated with tetrakis(triphenylphosphine)palladium (0) (23 mg, 0.020 mmol). The reaction mixture was purged with argon again, securely capped, and placed in a 105C oil bath for 2 h 45 min. The reaction mixture was cooled to room temperature, then diluted with DMF (4 mL). The resulting solution was filtered through a 0.45 uM frit attached to a single-use Waters C-18 sep-pak light cartridge (part No.WAT023501), and then purified by preparative HPLC (Condition A) using aPhenomenex Luna Axia 30 x 100 mm S10 column from 20% Solvent B to 85% Solvent B over 12 min, ret. T = 4.84 min to afford the title compound (12 mg, 31%) as a white solid. ¾ NMR (500 MHz, DMSO-d6) delta ppm 3.91-3.97 (m, 3 H), 4.04 (d, J=7.93 Hz, 2 H), 7.35 (d, J=3.36 Hz, 1 H), 7.49-7.58 (m, 1 H), 7.79-7.86 (m, 2 H), 8.40-8.47 (m, 1 H), 8.59-8.68 (m, 3 H), 8.78-8.85 (m, 2 H). LC/MS (Condition B): ret. T = 2.0min, (M+H)+ 382.04. Analytical HPLC: (Condition A): >97%, ret. T = 16.13 min, (Condition B):>97%, ret. T = 18.28 min, (Condition C): >98%, ret. T = 5.96 min, (Condition D): >98%, ret. T = 6.61 min.

According to the analysis of related databases, 89640-55-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; VELAPARTHI, Upender; FRENNESSON, David B.; SAULNIER, Mark G.; AUSTIN, Joel F.; HUANG, Audris; BALOG, James Aaron; VYAS, Dolatrai M.; WO2012/9510; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 109306-86-7, 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. 109306-86-7, name is 2-(2-Bromophenyl)pyridine, molecular formula is C11H8BrN, 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.

General procedure: Process (i) A dry 50-mL two-necked round bottom flask equipped with a glass stopper and a three-way stopcock was charged with 2-(2-chlorophenyl)pyridine (1.20 g, 6.32mmol) and CH2Cl2 (10 mL). The resulting colorless solution was cooled to 0 C, and mCPBA (1.64 g, 9.50mmol) was added slowly. The temperature was gradually raised to rt, and the colorless solution was stirred for 6 h. Cooling again to 0 C, 1M aq NaOH (10 mL) was slowly added. The organic layer was washed with 1M aq NaOH (10 mL) and brine (10 mL), and then dried over Na2SO4 (10 g). Filtration followed by evaporation gave nearly pure 2-(2-chlorophenyl)-pyridine-N-oxide (1.28 g) as a yellow oil. This was used for the next reaction without further purification.

According to the analysis of related databases, 109306-86-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tanaka, Shinji; Suzuki, Yusuke; Kimura, Takahiro; Kitamura, Masato; Bulletin of the Chemical Society of Japan; vol. 92; 10; (2019); p. 1707 – 1720;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem