Month: April 2022

Application of 84199-61-1 ,Some common heterocyclic compound, 84199-61-1, molecular formula is C7H6BrNO, 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.

Synthesis of 7-(3,4,5-trimethoxyphenyl)quinolin-5-ol (6.2) for Examples 2, 3, 4, 5, 9, 18, 23[0276] 3-Acetyl-2-bromopyridine, 140 mg 5-ethynyl-1,2,3-trimethoxybenzene 2.1, 101 muL triethylamine, 17 mg triphenylphosphinpalladium(II) chlorid, 1 mg Cu(I)I were suspended in 4 mL THF under argon atmosphere and stirred for 1 h at 25 C. The mixture was diluted with DCM and extracted with diluted aq. NH3 and saturated NH4Cl solution. The organic phase was concentrated and the mixture separated via FCC (10 g SiO2, Cyclohexane?cyclohexane/ethylacetate 70:30) to yield 90 mg 1-(2-(3,4,5-trimethoxyphenylethynyl)pyridin-3-yl)ethanone as solid. Analysis: HPLC-MS: Rt=1.21 min (method E) M+H=312.

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. 84199-61-1, 3-Acetyl-2-bromopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOFFMANN, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KLICIC, Jasna; SCHAENZLE, Gerhard; WOLLIN, Stefan Ludwig Michael; CONVERS-REIGNIER, Serge Gaston; EAST, Stephen Peter; MARLIN, Frederic Jacques; McCARTHY, Clive; SCOTT, John; US2013/29949; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1003711-43-0, 2-Bromo-5-hydroxy-3-methylpyridine, 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 C6H6BrNO, blongs to pyridine-derivatives compound. Computed Properties of C6H6BrNO

(A) A mixture of 6-bromo-5-methylpyridin-3-ol (1 g, 5.32 mmol), 1-bromo-2-methoxyethane (730 mg, 5.25 mmol) and K2CO3 (1.5 g, 10.87 mmol) in MeCN (20 mL) was stirred at rt overnight, after which the reaction was quenched by the addition of water (100 mL). The resulting solution was extracted with EtOAc (2*100 mL) and the combined organic phase was dried (Na2SO4) and concentrated under reduced pressure. The resultant residue was purified by silica gel chromatography (0-15% EtOAc/petroleum ether) to afford 2-bromo-5-(2-methoxyethoxy)-3-methylpyridine (500 mg, 38%) as colorless oil. LC/MS: mass calcd. for C9H12BrNO2: 246.10, found: 246.0 [M]+, 248.0 [M+2]+.

The synthetic route of 1003711-43-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; Liang, Yin; Demarest, Keith T.; (109 pag.)US2017/290800; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 22282-96-8, 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. 22282-96-8, name is 2-Bromo-6-methyl-5-nitropyridine, molecular formula is C6H5BrN2O2, 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 suspension of 6-bromo-2-methyl-3-nitropyridine (XIV) (250 g, 1.15 mol, 1.00 eq) and NH4C1 (300 g, 5.61 mol, 4.88 eq) in EtOH (3.50 L) and water (150 mL) was heated with stirring to 65C. To this mixture was added Fe (130 g, 2.33 mol, 2.02 eq) and HC1 (15.3 g, 419 mmol, 0.36 eq). The suspension was then heated to 80C for another 3 h. The reaction was cooled to 25C and filtered through a plug of Celite. The filtrate was concentrated under reduced pressure to yield a residue that was taken up in EtOAc (1 L x 3) and washed with brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give 6-bromo-2-methylpyridin-3-amine (XV) as brown solid (373 g, 1.99 mol, 86.7% yield) which was used for the next step without any purification. l NMR (DMSO- tf, 400 MHz) delta ppm 6.01 (dd, J = 2.3, 7.9 Hz, 2H), 7.03 (d, J = 8.2 Hz, 1H); ESIMS found for C6H7BrN2 mlz 186.8 (M+H).

According to the analysis of related databases, 22282-96-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (247 pag.)WO2017/24004; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1083057-12-8, 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 1083057-12-8, name is tert-Butyl 3-(3-methylpyridin-2-yl)benzoate. This compound has unique chemical properties. The synthetic route is as follows.

tert-Butyl-3-(3-methylpyridin-2-yl)benzoate (1.0 eq) is dissolved in EtOAc (6 vol). Water (0. 3 vol) is added followed by urea-hydrogen peroxide (3 eq). The phthalic anhydride (3 eq) is added portion-wise as a solid to maintain the temperature in the reactor below 45 0C. After completion of phthalic anhydride addition, the mixture is heated to 45 0C. After stirring for an additional 4 hours, the heat is turned off. 10% w/w aqueous Na2SO3 (1.5 eq) is added via addition funnel. After completion of Na2SO3 addition, the mixture is stirred for an additional 30 minutes and the layers separated. The organic layer is stirred and 10% w/w aq. Na2Ctheta3 (2 eq) is added. After stirring for 30 minutes, the layers are allowed to separate. The organic phase is washed 13% w/v aq NaCl. The organic phase is then filtered and concentrated to afford crude 2-(3-(tert-butoxycarbonyl)phenyl)-3-methylpyridine-l -oxide (95%) that is used directly in the next step.

According to the analysis of related databases, 1083057-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2009/73757; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 63237-88-7 , The common heterocyclic compound, 63237-88-7, name is Pyrazolo[1,5-a]pyridine-2-carboxylic acid, molecular formula is C8H6N2O2, 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 132N-((ls,4s)-4-(5-fluoro-2-(4′-(3-(piperazin-l-yl)propyl)biphenyl-3- yloxy)nicotinamido)cyclohexyl)pyrazolo [ 1 ,5-a] pyridine-2-carboxamide To a solution of tert-butyl 4-(3-(3′-(3-((ls,4s)-4-aminocyclohexylcarbamoyl)-5-fluoropyridin- 2-yloxy)biphenyl-4-yl)propyl)piperazine-l-carboxylate (150 mg, 0.24 mmol) in acetonitrile (2 mL) was added pyrazolo[l,5-a]pyridine-2-carboxylic acid (38.5 mg, 0.24 mmol) and triethylamine (0.331 mL, 2.37 mmol). 1-Propanephosphonic acid cyclic anhydride, 1.57M solution in THF (0.159 mL, 0.25 mmol) was then added and the mixture stirred at RT for 1 h. The mixture was poured into sat NaHCO3 (aq) and the organics extracted into EtOAc (x2). The extractions were combined, dried (MgSO4) and evaporated to give a residue. This was dissolved in dichlormethane (2mL) to which TFA (2mL) was added and the mixture stirred at RT for 20 min. The solvents were removed in vacuo and the residue dissolved in methanol and purified using reverse phase preparative chromatography using eluent = TFA(aq)/MeOH. The appropriate fractions were combined and evaporated to give a residue which on trituration with ether gave a solid. The solid was dried overnight under vacuum at 40 0C to give the title compound. Yield: 58 mg1H NMR (400 MHz, CD3OD) delta 8.49 (d, J= 7.2 Hz, IH), 8.41 (d, J= 6.9 Hz, IH), 8.12 (d, J = 3.1 Hz, IH), 8.07 (dd, J= 7.9, 3.1 Hz, IH), 7.66 (d, J= 9.0 Hz, IH), 7.50 – 7.45 (m, 4H), 7.42 – 7.41 (m, IH), 7.25 – 7.20 (m, IH), 7.18 – 7.13 (m, 3H), 6.96 – 6.92 (m, 2H), 4.17 – 4.12 (m, IH), 4.04 – 3.98 (m, IH), 3.41 (t, J= 5.4 Hz, 4H), 3.24 – 3.19 (m, 4H), 2.94 – 2.89 (m, 2H), 2.64 (t, J= 7.6 Hz, 2H), 1.99 – 1.68 (m, 10H). MS: [M+H]+=676 (calc=676) (MultiMode+)

The synthetic route of 63237-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/144494; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 204378-41-6, 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. 204378-41-6, name is Methyl 6-chloro-4-methoxypicolinate, molecular formula is C8H8ClNO3, 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.

(2) Synthesis of 6-chloro-4-methoxypicolinic Acid [Compound (II-75)] Using 6-chloro-4-methoxypicolinic acid methyl ester [Compound (V-75)] (0.5 g, 2.48 mmol), the Compound (II-75) was synthesised according to the process of Synthesis Example 20 (3). White solid, yield: 0.45 g, percent yield: 97.0%, m.p.: 183-185 C. IR KBr cm-1: 1707, 1599, 1473, 1320, 1284, 1107, 1038, 921, 870, 723. 1H-NMR (60 MHz, d6-DMSO, delta): 3.84 (3H, s, OCH3), 6.94 (1H, d, J=2 Hz, pyridine ring H), 7.45 (1H, d, J=2 Hz, pyridine ring H), COOH indistinctness.

According to the analysis of related databases, 204378-41-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kureha Kagaku Kogyo K.K.; US6610853; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1122-43-6, 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 1122-43-6, name is 2,6-Dimethyl-3-hydroxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of the 2,6-dimethylpyridin-3-ol (500 mg,4.06 mmol) in DMF (15 mL) in a 50 mL flame-dried RBF, K2CO3(0.617 g, 4.47 mmol) and MOM-Cl (0.37 mL, 4.87 mmol) wereadded successively. The solution was stirred at RT overnight. Water(30 mL) was added and the reaction mixture extracted with EtOAc(2 20 mL). The organic layer was washed with cold water (2 30 mL) and brine (30 mL) and dried over magnesium sulfate andconcentrated under reduced pressure

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 1122-43-6, 2,6-Dimethyl-3-hydroxypyridine.

Reference:
Article; Xu, Qian; Kulkarni, Amol A.; Sajith, Ayyiliath M.; Hussein, Dilbi; Brown, David; Guener, Osman F.; Reddy, M. Damoder; Watkins, E. Blake; Lassegue, Bernard; Griendling, Kathy K.; Bowen, J. Phillip; Bioorganic and Medicinal Chemistry; vol. 26; 5; (2018); p. 989 – 998;,
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. 936011-17-5, name is 5-Bromo-2-methoxyisonicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

Step B: methyl 4-formyl-6-methoxynicotinate (39-2)To a solution of compound 39-1 (30 g, 139 mmol) and Et3N (27 g, 280 mmol) in 100 mL of methanol was added Pd(dppf)C12 (10.5 g, 139 mmol). The resulting mixture was stirred underCO (50 Psi) at 70 C for 12 hours. After cooling, filtration and concentration, the resulting residue was purified by column chromatography on silica gel (eluted with petroleum ether:ethyl acetate= 3:1) to give 39-2. MS(ESI) mle (M+Hj: 196.0.

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, 936011-17-5, 5-Bromo-2-methoxyisonicotinaldehyde.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HAGMANN, William, K.; NARGUND, Ravi, P.; BLIZZARD, Timothy, A.; JOSIEN, Hubert; BIJU, Purakkattle; PLUMMER, Christopher, W.; DANG, Qun; LI, Bing; LIN, Linus, S.; CUI, Mingxiang; HU, Bin; HAO, Jinglai; CHEN, Zhengxia; WO2014/22528; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1443759-42-9 ,Some common heterocyclic compound, 1443759-42-9, molecular formula is C8H10N2O3, 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.

36.3: 4-Bromo-6-methoxy-pyridine-2-carboxylic acid methyl ester To a mixture of 3.47 mL (29.3 mmol) tert-butyl nitrite and 6.60 g (29.3 mmol) copper(II)bromide in 120 mL acetonitrile was added a solution of 3.33 g (18.3 mmol) 4-amino-6-methoxy-pyridine-2-carboxylic acid methyl ester in 30 mL acetonitrile dropwise at 40 C. This mixture was stirred at 80 C. for 1 h, then poured into ice water. The precipitate was filtered off, washed with water and dried. The crude material was purified by flash chromatography (PE/EtOAc=4/1?3/1). yield: 2.50 g (56%) ESI-MS: m/z=246 (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,1443759-42-9, its application will become more common.

Reference:
Patent; HEIMANN, Annekatrin; DAHMANN, Georg; GRUNDL, Marc; MUELLER, Stephan Georg; WELLENZOHN, Bernd; US2013/158042; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1017183-06-0, 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 1017183-06-0, name is 2-Methyl-3-(pyridin-2-yl)propanoic acid. This compound has unique chemical properties. The synthetic route is as follows.

DIPEA (63.6 mu, 0.365 mmol) was added to a mixture of 2-methyl-3-(pyridin-2- yl)propanoic acid (60.4 mg, 0.365 mmol), 4-(3,5-dimethylisoxazol-4-yl)-Nl- (tetrahydro-2H-pyran-4-yl)benzene-l,2-diamine (100 mg, 0.348 mmol) and 2-(3H- [l,2,3]triazolo[4,5-b]pyridin-3-yl)-l, l,3,3-tetramethylisouronium hexafluorophosphate(V) (139 mg, 0.365 mmol) in DMF (lmL). The reaction mixture [ 5 was stirred at rt for 18h. DCM (lOmL) and saturated sodium bicarbonate solution (5mL) were added and the reaction mixture shaken thoroughly. The organic phase was collected, washed with brine (lOmL) and collected via PhaseSep cartridge. The solvent was removed in vacuo to afford a loose brown solid, which was redissolved in acetic acid (lmL) and heated to 80C with stirring for 72h. After cooling to rt, methanol 10 (5mL) was added and the solution was treated to SCX chromatography; eluting the compound with 1% ammonia in methanol solution. The ammoniacal eluent was concentrated in vacuo and the crude residue was purified by chromatography (4g silica, 0-10% methanol in DCM, gradient elution) to afford 3,5-dimethyl-4-(2-(l-(pyridin-2- yl)propan-2-yl)-l-(tetrahydro-2H-pyran-4-yl)-lH-benzo[d]imidazol-5-yl)isoxazole (20 15 mg, 13%) as an off white solid; Rt 1.29 min (Method 1), m/z 417 (M+H)+ (ES+); 1H MR (d6-DMSO) delta: 8.49 (ddd, J = 4.8, 1.9, 0.9 Hz, 1H), 7.71 – 7.55 (m, 3H), 7.26 – 7.08 (m, 3H), 4.71 (dd, J = 13.6, 9.4 Hz, 1H), 4.14 – 3.88 (m, 3H), 3.64 – 3.45 (m, 2H), 3.43 – 3.26 (m, 28H), 3.20 – 3.08 (m, 2H), 2.39 (s, 4H), 2.22 (s, 3H), 1.78 (d, J = 12.8 Hz, 1H), 1.48 – 1.31 (m, 4H)

According to the analysis of related databases, 1017183-06-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CELLCENTRIC LTD; PEGG, Neil Anthony; TADDEI, David Michel Adrien; ONIONS, Stuart Thomas; TSE, Eric Sing Yuen; BROWN, Richard James; MYCOCK, David Kenneth; COUSIN, David; PATEL, Anil; (135 pag.)WO2016/170324; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem