936011-17-5 | Page 2 of 3 | Pyridine-derivatives

The origin of a common compound about 936011-17-5

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.

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 936011-17-5, name is 5-Bromo-2-methoxyisonicotinaldehyde. A new synthetic method of this compound is introduced below., name: 5-Bromo-2-methoxyisonicotinaldehyde

Step 2: ethyl (2 E )-3-(5-bromo-2-methoxypyridin-4-yl)acrylate; 5 To solution of 5-bromo-2-methoxyisonicotinaldehyde (1 eq.) from step 1 and triethylphosphonoacatate (1.1 eq.) at O0C was added potassium tert-butoxide (1.0M in THF; l.leq.). The reaction mixture was allowed to warm to room temperature and stirred for Ih. The reaction was quenched with saturated aqueous NH4Cl and then extracted with EtOAc. The organic extract was washed with saturated NaHCO3, brine, dried over MgSO4, filtered and concentrated. Purification by column chromatography on silica gel (Combi-Flash by ISCO), eluting with Hex/EtOAc (O to 50% in 30min) afforded the desired compound.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2009/23964; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Analyzing the synthesis route of 5-Bromo-2-methoxyisonicotinaldehyde

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.

Synthetic Route of 936011-17-5, Adding some certain compound to certain chemical reactions, such as: 936011-17-5, name is 5-Bromo-2-methoxyisonicotinaldehyde,molecular formula is C7H6BrNO2, 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 936011-17-5.

5-Bromo-2-methoxypyridine-4-carbaldehyde (25 g, 115.5 mmol, 1 eq.) Was dissolved in 500 ml of dichloromethane, and the temperature was lowered to -78 C. Under the protection of nitrogen,Diethylaminosulfur trifluoride (74.5g, 462mmol, 4eq.) Was added dropwise.After the dropwise addition, the reaction was carried out at 21 C for 16 hours.After the reaction, drop the reaction drop into ice water,Make alkaline with saturated sodium bicarbonate solution.It was extracted with dichloromethane, and the organic phase was concentrated and then subjected to column chromatography to obtain 25.3 g of white solid 5-bromo-4- (difluoromethyl) -2-methoxypyridine in 92% yield.

Reference:
Patent; Ali Biological New Materials (Changzhou) Co., Ltd.; Shi Jianyun; Xu Yibo; Dai Hongsheng; Zhou Chao; (8 pag.)CN110734397; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Analyzing the synthesis route of 5-Bromo-2-methoxyisonicotinaldehyde

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.

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, Quality Control of 5-Bromo-2-methoxyisonicotinaldehyde, blongs to pyridine-derivatives compound. Quality Control of 5-Bromo-2-methoxyisonicotinaldehyde

The solution of 5-bromo-2-methoxy-pyridine-4-carbaldehyde (CAS: 936011-17-5, Vendor: Bide, 25.00 g, 115.72 mmol) and ammonium acetate (4.46 g, 57.86 mmol) in nitroethane (150 mL) was stirred at 100 C for 16 hrs. After being cooled down, the mixture was concentrated and purified by flash column (PE/EA = 10/1) to give compound 70a (23.00 g) as a green solid. MS: calc?d 273 (MH+), measured 273 (MH+).

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.; DEY, Fabian; KOU, Buyu; LIU, Haixia; SHEN, Hong; WANG, Xiaoqing; ZHANG, Weixing; ZHANG, Zhisen; ZHANG, Zhiwei; ZHU, Wei; (203 pag.)WO2019/238616; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Some scientific research about 5-Bromo-2-methoxyisonicotinaldehyde

General procedure: In a round-bottom flask, to aldehyde (1.0 mmol) in DMF(1 mL) was added sulfinamide (2 or 2a) (1.5 mmol) followed by DBU (1.5 mmol). The solution was allowed to stirat room temperature for 2-10 h. The progress of the reaction was monitored by TLC. After complete conversion, the reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated. The crude product was subjected to column chromatography on silica gel (eluent:petroleum ether/ethyl acetate = 80:20) to provide the corresponding N-sulfinyl imines.

Reference:
Article; Ramaiah, Manjunatha M; Shubha, Priya Babu; Prabhala, Pavan Kumar; Shivananju, Nanjunda Swamy; Journal of Chemical Research; vol. 44; 1-2; (2020); p. 72 – 79;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Some scientific research about 5-Bromo-2-methoxyisonicotinaldehyde

A new synthetic route of 5-Bromo-2-methoxyisonicotinaldehyde

The synthetic route of 936011-17-5 has been constantly updated, and we look forward to future research findings.

Application of 936011-17-5 , The common heterocyclic compound, 936011-17-5, name is 5-Bromo-2-methoxyisonicotinaldehyde, 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.

To the solution of 5-bromo-2-methoxy-pyridine-4-carbaldehyde (CAS: 936011-17-5, Vendor: Bidepharm, 25.0 g, 115.72 mmol) in methanol (500 mL) was added sulfuric acid (14.19 mL, 231.5 mmol). After being stirred at rt for 18 hrs, the mixture was concentrated and added to the mixture solvent of aq. Na2C03 (150 mL) and EA (150 mL). The mixture was separated, the organic layer was washed with brine (50 mL), dried over Na2S04 and concentrated to give compound 76a (28.0 g) as a yellow oil. MS: calc?d 262 (MH+), measured 262 (MH+).

The synthetic route of 936011-17-5 has been constantly updated, and we look forward to future research findings.

A new synthetic route of 5-Bromo-2-methoxyisonicotinaldehyde

The synthetic route of 936011-17-5 has been constantly updated, and we look forward to future research findings.

Simple exploration of 936011-17-5

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,936011-17-5, its application will become more common.

Electric Literature 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.

To the solution of 5-bromo-2-methoxy-pyridine-4-carbaldehyde (compound 74a, 25.00 g, 115.70 mmol) in THF (250 mL) was added MeMgBr (3M in 2-Me-THF, 50.20 mL, 150.40 mmol) drop wise at -78 C over 30 mins. After being stirred at -78 C for 0.5 h, the mixture was warmed to rt slowly and then quenched with 100 mL saturated NFLCl, diluted with 400 mL water and extracted with 150 mL EA twice. The combined organic layer was washed with 180 mL water and 100 mL brine, dried over Na2S04 and concentrated to give the cmde product compound 74b (27.00 g) as a yellow oil. MS calc?d 232 (MFL), measured 232 (MFL).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,936011-17-5, its application will become more common.

Extracurricular laboratory: Synthetic route of 5-Bromo-2-methoxyisonicotinaldehyde

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.

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

Introduction of a new synthetic route about 5-Bromo-2-methoxyisonicotinaldehyde

Synthetic Route 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.

To a stirred solution of 5-bromo-2-methoxyisonicotinaldehyde (1.45 g, 6.71 mmol) in nPrOH (60 mL) were added potassium vinyltrifluoroborate (0.899 g, 6.71 mmol), PdCl2(dppf) (98 mg, 0.134 mmol), and TEA (0.94 mL, 6.71 mmol). The reaction mixture was heated to reflux for 3 h, cooled to room temperature, diluted with EtOAc, and washed with water and brine. The organic layer was dried (Na2SO4), concentrated, and purified by flash chromatography to afford the title compound. 1H NMR (600 MHz, CDCl3) 6 10.08 (s, IH); 7.90 (d, IH); 7.70 (dd, IH); 6.93 (d, IH); 5.72 (d, IH); 5.43 (d, IH); 4.03 (s, 3H).

Reference:
Patent; MERCK & CO., INC.; WO2007/50383; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem