Day: March 9, 2022

Adding a certain compound to certain chemical reactions, such as: 89510-90-7, 2-Chloro-5-fluoro-4-pyridinamine, 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, Recommanded Product: 89510-90-7, blongs to pyridine-derivatives compound. Recommanded Product: 89510-90-7

Intermediate 11A was synthesized employing the procedure described for Example 7C (Scheme 7). The crude compound was purified by silica gel column chromatography eluted with 55% Ethylacetate in Hexane to afford hA (120 mg, 0.112 mmol, 19.3 % yield) as a off white solid. LCMS: m/z 622.7(M+H); rt 1.60 mm;10 Conditions B.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89510-90-7, 2-Chloro-5-fluoro-4-pyridinamine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HARIKRISHNAN, Lalgudi S.; FINK, Brian E.; BORZILLERI, Robert M.; TONUKUNURU, Gopikishan; WARRIER, Jayakumar Sankara; (111 pag.)WO2017/19757; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 13445-16-4, name is 3-Bromo-2,6-dimethoxypyridine, the common compound, a new synthetic route is introduced below. SDS of cas: 13445-16-4

EXAMPLE 1 Preparation of 2,6-dimethoxy-3-bromo-4-(diphenylphosphino)pyridine To a magnetically stirred solution of 4.0 mL of approximatly 2.0M LDA solution (in hexane) (7.98 mmol) was added a solution of 2,6-dimethoxyl-3-bromopyridine (3.14 g, 6.14 mmol) in 10 mL of THF at -78 C. over a period 20 minutes while the internal temperature was kept below -78 C. To the resulting red-brown suspension was added a solution of chlorodiphenylphosphine (1.20 mL, 6.75 mmol) in the 10 mL of THF at -78 C. The reaction mixture was allowed to warm to ambient temperature overnight and was poured into 20 mL water. The organic product was extracted with dichloromethane (3*20 mL). The combined extract was dried with anhydrous magnesium sulfate and was concentrated in vaccuo to give a crude product which was recrystallized in methanol to give 2.34 g of pure product (95% theoretical yield). 1 H-NMR(400 MHz): delta 3.83 (s, 3H, OCH3), 4.00 (s, 3H, OCH3), 5.71 (d, JPH =2.4 Hz, 1H, PyH’s), 7.38~7.28 (m, 10H, PhH’s). 31 P-NMR(161 MHz): delta-4.18 ppm. 13 C-NMR(101 MHz): delta 53.61, 54.48, 101.73 (J=27.8 Hz), 106.52 (J=2.1 Hz), 128.76 (J=7.6 Hz), 129.38, 134.07, 134.27, 134.33, 134.43, 154.13 (J=16.0 Hz), 158.62 (J=5.6 Hz), 161.5. mass spectrum (high resolution): M.W.=401.0, consistent with C19 H17 NPBrO2, melting point: 149.7~150.8 C.

The synthetic route of 13445-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Hong Kong Polytechnic University; US5886182; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 16744-81-3 ,Some common heterocyclic compound, 16744-81-3, molecular formula is C7H7NO2, 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.

D1. METHVL3- (4-METHOXVPVRIDIN-2-Y ACRVLATE; A mixture of 45 g OF 4-METHOXYPYRIDINE-2-CARBALDEHYDE (Ashimori et AL., Chem. Pharm. Bull. 38,2446- 2458 (1990) ), 75.80 g of pyridine hydrochloride, 102.45 g of monomethyl malonate potassium salt and 4.1 ml of piperidine in 700 ml of pyridine are slowly heated, with stirring, to 120°C. When the evolution of gas starts, the heating source is temporarily removed to stop the reaction from becoming too violent. Once the reaction has subsided, the mixture is stirred at 120°C for a further 2.5 hours, and the pyridine is then distilled off under reduced pressure. The residue is partitioned between ethyl ACETATE/WATER and the organic phase is washed with water and dried. The residue obtained after concentration is chromatographed on a silica gel column using ethyl acetate/petroleum ether 2: 1. This initially gives 43.2 g of the title compound as a yellow oil which crystallizes on standing and then shows a m. p. of 80-82°C. The mass spectrum shows the molecular peak MH+ at 194 Da

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. 16744-81-3, 4-Methoxypicolinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALTANA PHARMA AG; WO2005/30769; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 402-65-3, 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. 402-65-3, name is 2-Fluoroisonicotinic acid, molecular formula is C6H4FNO2, 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.

Intermediate 1; 3-[(2-Wi/oro-4-iodophenyl)amino]isonicotinic acid (R = Fluoro); A mixture of 2-fluoro-4-iodoaniline (20.0 g, 84.38 mmol) in dry THF (80 mL) was cooled to – 67 0C (dry ice/IPA bath) under nitrogen, prior to” slow addition of 1.0 M lithium bis(trimethylsilyl)amide (255 mL, 255 mmol) via addition funnel, at a rate that kept the internal temp below -59 0C (~2 h). After final addition, the yellow-green slurry was stirred for 30 min and then treated with 2-fluoroisonicotinic acid (8.0 g, 56.69 mmol). The bath was not removed, but the contents were allowed to slowly warm to room temp. After 4 days, the dark slurry was poured into a biphasic mixture of aqueous 2.0 lf sodium hydroxide (1000 mL) and ethyl acetate (150 mL). The aqueous layer was separated and the organics were again extracted with base (1000 mL). The pH of the two aqueous layers was adjusted to ~2 with concentrated hydrochloric acid. A yellow solid precipitated, which was filtered. The resultant yellow cake was washed with water (2 x 400 mL) and dried under high vacuum at 40 0C (17- 19 g). LC/MS [(5.2 min; 359 (M+1)].

According to the analysis of related databases, 402-65-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2006/45514; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 62135-58-4 ,Some common heterocyclic compound, 62135-58-4, molecular formula is C9H9N3O2, 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 stirred solution of ethyl [1,2,4]triazolo[1,5-a]pyridine-2-carboxylate (2.4 g, 12.55 mmol) in MeOH (20 mL) and THF (10 mL) was added NaBH4 (950 mg, 25.1 mmol) portionwise at 0 C. The mixture was stirred at RT for 2 h. The reaction mixture was quenched with saturated aqueous NH4Cl and concentrated in vacuo. The residue was dissolved in DCM/MeOH (100 mL), filtered, and the filter cake was rinsed with DCM/MeOH (50 mL). The combined filtrate was concentrated and purified by silica gel chromatography (EA/PE=1/1) to give [1,2,4]triazolo[1,5-a]pyridin-2-ylmethanol (1.6 g, yield: 85%) as a yellow solid. ESI-MS [M+H]+: 150.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62135-58-4, its application will become more common.

Reference:
Patent; Shire Human Genetic Therapies, Inc.; Papaioannou, Nikolaos; Fink, Sarah Jocelyn; Miller, Thomas Allen; Shipps, JR., Gerald Wayne; Travins, Jeremy Mark; Ehmann, David Edward; Rae, Alastair; Ellard, John Mark; (352 pag.)US2019/284182; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 936011-17-5, 5-Bromo-2-methoxyisonicotinaldehyde, 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, Recommanded Product: 5-Bromo-2-methoxyisonicotinaldehyde, blongs to pyridine-derivatives compound. Recommanded Product: 5-Bromo-2-methoxyisonicotinaldehyde

To a solution of 5-bromo-2-methoxy-pyridine-4-carbaldehyde (23.5 g, 108.8 mmol) in MeOH (100 mL) were successively added a solution of I2 (35.9 mg, 141.4 mmol) in MeOH (75 mL) and a solution of KOH (15.9 g, 282.8 mmol) in MeOH (75 mL) at 0 C. The resulting mixture was stirred for 1 hr at 0 C and the reaction was quenched with saturated aqueous NaHS03. The resulting mixture was diluted with DCM (400 mL). The separated organic phase was washed with H20 (150 mL) and brine (150 mL), dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by flash column (eluting with PE_EA=20: 1, v:v) to give methyl 5-bromo-2-methoxy-pyridine-4-carboxylate (14.9 g) as a light yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,936011-17-5, 5-Bromo-2-methoxyisonicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Jianhua; WANG, Min; YANG, Song; (81 pag.)WO2018/83136; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 188637-63-0 ,Some common heterocyclic compound, 188637-63-0, molecular formula is C6H7BrN2, 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 6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinic acid (582mg, 1.61 mmol) and 6-bromo-pyridin-2yl-methylamine (300mg, 1.61 mmol) in DMF was added CDI (261 mg, 1.61 mmol). The reaction mixture was stirred at r.t. for 2 h. The reaction mixture was purified on RP-HPLC to give N-((6-bromopyridin-2-yl)methyl)-6-(2- cyanophenyl)-2-(3-fluorophenethylamino)nicotinamide (700mg, 82%) LRMS (M+H+) m/z 530.1.

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. 188637-63-0, (6-Bromopyridin-2-yl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CYTOKINETICS, INCORPORATED; WO2008/16643; (2008); A2;,
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 824-52-2, name is 5-Methyl-1H-pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 5-Methyl-1H-pyrrolo[2,3-b]pyridine

Compound 3 (0.50 g, 3.8 mmol), methenamine (0.8 g, 5.7 mmol) was added to a three-necked flask,Water (5 mL) and acetic acid (2.5 mL);The reaction was heated to reflux for 4 hours. The reaction was cooled to room temperature and extracted with ethyl acetate (30 mL x 3); the organic phases were combined and washed with saturated brine (30 mL)Dry over sodium sulfate and filter. The filtrate was spin-dried, and the crude product was separated by silica gel column chromatography (petroleum ether: ethyl acetate = 1: 2 by volume)A pale yellow solid was obtained, compound 4 (0.3 g, 1.9 mmol, 49%)

With the rapid development of chemical substances, we look forward to future research findings about 824-52-2.

Reference:
Patent; Kanghua (Shanghai) Drug Discovery Co., Ltd.; Ma Jingxiang; (5 pag.)CN107056781; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 89809-65-4 ,Some common heterocyclic compound, 89809-65-4, 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.

6-Cyanonicotinic acid methyl ester (701 mg) was dissolved in a mixed solvent of methanol (1 ml) and tetrahydrofuran (7 ml) and sodium borohydride (197 mg) was added under icecooling. The mixture was directly heated to room temperature and stirred overnight. Water (20 ml) was added, and the mixture was extracted with ethyl acetate (once with 50 ml and once with 30 ml), washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified with column chromatography (Yamazen HI-FLASH COLUMN size 2L, elution solvent: hexane/ethyl acetate) to give the title compound (264 mg). 1H-NMR(CDCl3)delta:2.09(1H,m), 4.86(2H,d,J=5.1 Hz), 7.71(1H,d,J=8.1 Hz), 7.89(1H,dd,J=1.8 Hz,8.1 Hz), 8.70(1H,s). MS:135(M++1).

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. 89809-65-4, Methyl 6-Cyanopyridine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; EP2154135; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 131747-53-0, 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. 131747-53-0, name is (6-(Trifluoromethyl)pyridin-2-yl)methanol, molecular formula is C7H6F3NO, 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) 2-Chloro-4-((6-(trifluoromethyl)pyridin-2-yl)methoxy)pyridine 6-(Trifluoromethyl)-2-pyridinemethanol (2.20 g, 12.8 mmol) was reacted according to Example 113 (step c) to provide the title compound (3.30 g, 89%) as a white foam: ESI MS m/z 289 [M+H]+.

According to the analysis of related databases, 131747-53-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Albany Molecular Research, Inc.; SURMAN, Matthew D.; FREEMAN, Emily E.; GUZZO, Peter R.; HENDERSON, Alan J.; HADDEN, Mark; US2014/163012; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem