Tag: M.W:200-300

Synthetic Route of 1111637-94-5 , The common heterocyclic compound, 1111637-94-5, name is 5-Bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H7BrN2, 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 19 (50 mg, 0.2369 mmol) and 2 (50 mg, 0.2369 mmol) in ethanol and toluene (1:4 mL) was added sodium carbonate (49.74 mg, 0.4738 mmol). The reaction was degassed and purged with nitrogen for 15 min. Pd(dppf)Cl2.DCM (9.06 mg, 0.0114 mmol), and again degassed for 15 min. The reaction mixture was stirred for 2 h at 90 C. and the reaction mixture allowed to cool to rt and diluted with DCM (25 mL). The organic layer was filtered through Celite and concentrated to get the crude. The resulting oil was purified via silica gel chromatography using a gradient of 30% ethyl acetate:hexane to afford Compound 20. MS-ES+ 277 1H NMR (400 MHz, DMSO-D6) 20: 11.37 (d, 1H), 10.24 (d, 1H), 8.45 (d, 1H), 8.09 (d, 2H), 7.68 (d, 1H), 7.43 (d, 2H), 7.28 (d, 1H), 6.46 (d, 1H), 6.44 (d, 1H), 5.79 (d, 1H), 2.30 (d, 1H).

The synthetic route of 1111637-94-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRIEN PHARMACEUTICALS LLC; Vankayalapati, Hariprasad; Yerramreddy, Venkatakrishnareddy; Gangireddy, Paramareddy; Appalaneni, Rajendra P.; US2014/315909; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17570-98-8 , The common heterocyclic compound, 17570-98-8, name is 2-(Bromoacetyl)pyridine hydrobromide, molecular formula is C7H7Br2NO, 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 6; 1 -(4-(1 -f6-methylpyridin-3-yl)-4-(pyridin-2-vO-1 H-imidazol-2-yltohenyl)-1 H-pyrrolor2.3- bipyridi?e; A mechanically stirred suspension of N’-(6-methylpyridin-3-yl)-4-(1H-pyrrolo[2,3- b]pyridin-1-yl)benzamidine (49.6 g, 152 mmol) in anhydrous THF (1 L) was treated over 30 mi? at less than 40C with a solution of LiHMDS (350 mL of 1M in THF). After 15 mi? at 0 0C the clear brown solution was treated portionwise at 3-6 0C with 2-bromo-1-(pyridin-2- yl)ethanone hydrobromide (42.6 g, 152 mmol) over 20 min. After being stirred 30 min at 00C and the mixture was warmed to 25 0C over 1h and stirred at 25 0C for 30 min. Water (500 mL) and EtOAc (1L) were added and the organic layer was separated, washed with brine, dried over Na2SO4, and concentrated. The residue was dissolved in 200 mL acetic acid and the resulting solution heated at 95 0C for 20 min and concentrated. The residue was dissolved in EtOAc (1L) and 2N HCI (450 mL). The organic layer was separated and washed with water (150 mL) and aqueous 10% citric acid (250 mL). The citric acid layer was extracted with EtOAc (2 x 100 mL). The combined organic layers were washed with water, brine, dried, and concentrated giving 42 g of crude product as a brown oil which was purified by SGC (1% MeOH in DCM, 0.5 % NH4OH), giving the title substance in several fractions contaminated with 1-7% of the corresponding amide <4-(1H-pyrrolo[2,3-b]pyridin-1- yl)benzamide) as determined by HPLC (280 nM absorption ratio). Yield 15 g, 31%. The material was efficiently further purified by recrystallization as illustrated: a 4.5 g fraction containing 3.5% amide impurity was dissolved in 98:2 acetonitrile:water and the resulting solution stirred at RT fro 40 min. The crystalline precipitate was filtered, washed with fresh acetonitrile and dried giving 2.9 g of the title substance containing 0.3% amide. In this manner the remaining fractions were purified and the recrystallized solids combined giving 9.35 g of the title substance containing less than 1% amide impurity. 1H NMR (CDCI3) delta 8.58 (m, 2H), 8.37 (dd, 1H, J = 1.5, 4.8 Hz), 8.16 (d, 1H1 J = 7.9 Hz)1 7.97 (dd, 1H, J = 1.7, 7.9 Hz), 7.91 (br, 1H)1 7.82 (m, 2H)1 7.79 (td, 1H1 J = 1.7, 7.9 Hz), 7.62 (m, 2H)1 7.53-7.50 (m, 2H)1 7.24-7.19 (m, 2H), 7.15 (dd, 1H, J = 4.6. 7.9 Hz), 6.65 (d, 1 H, J = 3.7 Hz), 2.64 (s, 3H). MS (AP+) m/e 429 (MH+). Anal. Calcd for C27H20N6: C1 75.68; H1 4.70; N1 19.61. Found: C1 75.39; H1 4.52; N1 19.64. ICs0 = <3.21 nM The synthetic route of 17570-98-8 has been constantly updated, and we look forward to future research findings. Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/4117; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 234108-73-7 ,Some common heterocyclic compound, 234108-73-7, molecular formula is C10H13ClN2O2, 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 4-amino-2-chloropyridine (1.28 g, 10 mmol) and di-tert-butyl dicarbonate (2.21 g, 10.1 mmol) in TEtaF (20 mL) was cooled to O0C and a solution of IM lithium bis(trimethylsilyl)amide in TEtaF ( 20 mL, 20 mmol) was added slowly maintaining the temperature below O0C. The reaction was allowed to warm to room temperature over one hour and then quenched by the addition of 1.5 N aqueous ammonium chloride (15 mL). The mixture was extracted into ethyl acetate, washed with brine and the organic layer was dried (Na2SO4), filtered and evaporated. The residue was triturated with diethyl ether give pure tert-butyl (2-chloropyridin-4-yl)carbamate. The mother liquors were chromatographed on silica gel eluting with 25 – 45% ethyl acetate/ hexane to afford more product.A solution of tert-butyl (2-chloropyridin-4-yl)carbamate (1.14 g, 5 mmol) in dry TBDF (20 rriL) was cooled to -700C under an inert atmosphere and 1.7 M t-butyl lithium/pentane (8 mL, 13.5 mmol) was slowly added. The reaction was stirred for two hours and then dry DMF (1.2 mL, 15.5 mmol) was added. The reaction was allowed to slowly warm to room temperature over a three hour period. The reaction mixture was quenched with 3 N HCl (12 mL) and diluted with diethyl ether. The ether layer was washed with aqueous NaHCtheta3, dried (over Na2SO4), filtered and evaporated. The residue was triturated with cold diethyl ether to give pure t-butyl (2-chloro-3-formylpyridm-4-yl)carbamate. The mother liquors were chromatographed on silica gel eluting with 15-20% ethyl acetate/hexane to give additional product. lH-NMR(500 MHz, CDCI3): delta 11.0 (IH, br s), 10.52 (IH, s), 8.38 (IH, d, J= 6 Hz),8.31 (IH, d, J= 6 Hz), 1.54 (9H, s); m/e (m+1): 257.2.

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. 234108-73-7, tert-Butyl 2-chloropyridine-4-carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; WO2006/135627; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 727356-19-6 ,Some common heterocyclic compound, 727356-19-6, molecular formula is C6H5BrClN, 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 2; Preparation of 1-[5-(6-bromopyridin-2-yl)thiazol-2-yl]piperidin-4-yl}acetic acid tert-butyl ester (1-Thiocarbamoylpiperidin-4-yl)acetic acid tert-butyl ester (11.95 g, 46.3 mmol) obtained in Step 1 was added to a solution of 2-bromo-6-chloromethylpyridine (9.55 g, 6.3 mmol) obtained in Step 1 of Example 1 in ethanol (100 ml), and the mixture was heated at reflux overnight. The reaction solution was cooled to room temperature; dimethylformamide dimethylacetal (added 9.3 ml, 69.4 mmol) and triethylamine (19 ml, 139 mmol) were added and heated at reflux for 2 hours. After the reaction solution was concentrated, water was added, and it was extracted with ethyl acetate and washed with a saturated brine. The organic layer was dried over magnesium sulfate and the residue obtained by vacuum concentration was purified by chromatography on silica gel (n-hexane:ethyl acetate=50:50 to 0:100) and the title compound was obtained (13.09 g, 65%). 1H-NMR (400 MHz, DMSO-d6) delta: 7.95 (1H, s), 7.80 (1H, d, J=7.8 Hz), 7.67 (1H, t, J=7.8 Hz), 7.36 (1H, d, J=7.8 Hz), 4.02-3.95 (2H, m), 3.14-3.08 (2H, m), 2.20 (2H, d, J=7.2 Hz), 2.00-1.89 (1H, m), 1.79-1.72 (2H, m), 1.42 (9H, s), 1.34-1.21 (2H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,727356-19-6, its application will become more common.

Reference:
Patent; JAPAN TOBACCO INC.; US2006/205731; (2006); 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. 89415-54-3, name is 5-Bromo-N2-methylpyridine-2,3-diamine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 5-Bromo-N2-methylpyridine-2,3-diamine

Production Example 42A mixture of 5-bromo-N2-methylpyridin-2 , 3-diamine (0.70 g) , 2-ethylsulfanylbenzoic acid (0.66 g) , SC (0.80 g) , HOBt (23 mg) , and pyridine (20 ml) was stirred under reflux at 120 C for 30 minutes. After the reaction mixture was allowed to stand overnight, the mixture was stirred under reflux at 120 C for 9.5 hours again. Into the reaction mixture cooled to room temperature, water was poured under ice-cooling, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. A mixture of the resulting residue and acetic anhydride (7 ml) was stirred under reflux at 140 C for 1 hour. Aqueous sodium hydroxide solution was added to the reaction mixture cooled to room temperature to neutralize, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.60 g of 6-bromo-2- (2- ethylsulfanylphenyl ) -3-methyl-3H-imidazo [ 4 , 5-b] pyridine (hereinafter referred to as Present Compound 42) .Present Compound 421H-NMR (CDC13) delta : 8.47 (lH,d), 8.22 (lH,d), 7.54-7 (2H,m), 7.45-7.42 (lH,m), 7.37-7.32 (lH,m), 3.71 (3H, 2.86 (2H, q ) , 1.23 (3H,t)

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, 89415-54-3, 5-Bromo-N2-methylpyridine-2,3-diamine.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; TAKYO, Hayato; TAKAHASHI, Masaki; TANABE, Takamasa; NOKURA, Yoshihiko; ITO, Mai; IWATA, Atsushi; WO2012/86848; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 6945-67-1, 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 6945-67-1, name is 2-Bromo-4-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

The crude title compound from Step A above was dissolved in a mixture of degassed 1,4- dioxane (8.6 mL) and water (2 mL) in a microwave vial. Then [1 ,1 – bis(diphenylphosphino)ferrocene]dichloro-palladium(ll), complex with dichloromethane (0.034 g, 0.04 mmol), 2-bromo-4-nitropyridine (0.1 g, 0.49 mmol) and cesium carbonate (0.266 g, 0.82 mmol) were added and the reaction mixture was heated at ~115C in a sand- bath for 6 hours. The reaction mixture was diluted with ethyl acetate (100 mL) and water (30 mL), the organic phase separated, dried over Na2S04, filtered and the solvents evaporated in vacuo. The dark residue was purified by chromatography on silica (25 g puriFlash, Interchim) using a Biotage Isolera system employing an ethyl acetate/n-heptane gradient (5/95 -> 100/0 -> 100/0) to afford a mixture of the title compound and byproducts (0.076 g). Step C (0435) The mixture of the title compound from Step B above and byproducts (0.076 g) was dissolved in dichloromethane (10 mL) and trifluoroacetic acid (2.4 mL) was added. The reaction mixture was stirred at room temperature for 6 hours and then methanol was added (10 mL). The solvents were evaporated in vacuo and the residue suspended in methanol (10 mL). The solvents were again evaporated in vacuo and the residue suspended in dichloromethane (4 mL). After the addition of triethylamine (2 mL, 14.4 mmol), di-tert-butyl dicarbonate (0.2 g, 0.86 mmol), and 4-(dimethylamino)-pyridine (0.0036 g, 0.028 mmol), the reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate (100 mL) and water (40 mL). The organic phase was separated, dried over Na2S0 , filtered and the solvents removed in vacuo. The residue was purified on silica (25 g puriFlash, Interchim) using a Biotage Isolera One purification system employing an ethyl acetate/n-heptane gradient (5/95 -> 100/0 -> 100/0) to afford the Comparative Example C9 (F-9) Precursor and the byproduct as ~1.1-mixture (0.0231 g, pale yellow solid). 1H-NMR (400 MHz, CDCI3) delta = 9.38 (d, 1 H), 9.35 (d, 1 H), 9,31 (s, 2Eta), 9.02 (d, 1 H), 8.76- 8.70 (m, 5H), 8.68 (d, 1 H), 8.55 (d, 1 H), 8.43-8.37 (m, 3H), 8.12 (dd, 1 H), 8.07 (dd, 1 H), 7.43 (d, 1 H), 7.41 (d, 1 H), 1.82 (s, 18H) (0436) MS (ESI): m/z = 291.94 [MH-Boc of the title compound]*, 170.04 [MH+-Boc of byproduct]*

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 6945-67-1, 2-Bromo-4-nitropyridine.

Reference:
Patent; AC IMMUNE S.A.; PIRAMAL IMAGING SA; KROTH, Heiko; MOLETTE, Jerome; DARMENCY, Vincent; SCHIEFERSTEIN, Hanno; MUeLLER, Andre; SCHMITT-WILLICH, Heribert; BERNDT, Mathias; ODEN, Felix; GABELLIERI, Emanuele; (93 pag.)WO2018/15549; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 69045-83-6 , The common heterocyclic compound, 69045-83-6, name is 2,3-Dichloro-5-(trichloromethyl)pyridine, molecular formula is C6H2Cl5N, 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.

The chlorinated 2,3-dichloro-5-trichloromethylpyridine was put into a fluorination kettle (about 2300 kg).Injecting catalyst into the reaction fluorineAntimony pentafluoride 200kg,Add 1700kg of anhydrous hydrogen fluoride,The molar ratio of 2,3-dichloro-5-trichloromethylpyridine to hydrogen fluoride is 1:10.Excessive hydrogen fluoride facilitates the reaction.Turn on the reactor and stir, heat up and keep at 180 C.The reaction was carried out at a pressure of 6 MPa for 24 hours, and the temperature was lowered to 60 C.Transfer the material to 3000L in advanceWater in the washing kettle,The material is washed twice and then neutralized to a pH of 7,The material is then layered into a rectification tank.The mixture was subjected to vacuum distillation to obtain 2-fluoro-3-chloro-5-trifluoromethylpyridine having a content of ?99%.

The synthetic route of 69045-83-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Huimeng Biological Technology Co., Ltd.; Xiao Caigen; Liu Shuwen; (7 pag.)CN107935920; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 777931-67-6, 3-Bromo-2-chloro-6-methoxypyridine, 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, 777931-67-6, blongs to pyridine-derivatives compound. SDS of cas: 777931-67-6

D) 2-chloro-3-(2-fluoro-5-methoxyphenyl)-6-methoxypyridine Under an argon atmosphere, to a solution of 3-bromo-2-chloro-6-methoxypyridine (4.61 g) in toluene (60 mL) were added (2-fluoro-5-methoxyphenyl)boronic acid (3.52 g), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II)dichlorome thane adduct (1.69 g) and 2.0 M aqueous sodium carbonate solution (31.1 mL), and the mixture was stirred at 80C for 1 hr. Water was added at room temperature, and the reaction mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (4.06 g) as a white amorphous solid. 1H NMR (300 MHz, DMSO-d6) delta 3.77 (3H, s), 3.91 (3H, s), 6.90-6.94 (1H, m), 6.96 (1H, d, J = 8.3 Hz), 6.98-7.06 (1H, m), 7.24 (1H, t, J = 9.1 Hz), 7.80 (1H, d, J = 8.3 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,777931-67-6, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; MIWATASHI, Seiji; SUZUKI, Hideo; OKAWA, Tomohiro; MIYAMOTO, Yasufumi; YAMASAKI, Takeshi; HITOMI, Yuko; HIRATA, Yasuhiro; SHIBUYA, Akito; EP2816023; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1111637-74-1, 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 1111637-74-1, name is 1-(5-Bromo-2-fluoropyridin-3-yl)ethanone. This compound has unique chemical properties. The synthetic route is as follows.

Step 3: (R)-5-Amino-3-(5-bromo-2-fluoropyridin-3-yl)-3,6,6-trimethyl-3,6-dihydro-2H-1,4-thiazine 1,1-dioxide In an analogous sequence of reactions to those described for Example 7, steps 1-4, 1-(5-bromo-2-fluoropyridin-3-yl)ethanone (11 g, 50 5 mmol) was converted to the title compound in 20% yield. LC/MS (ESI+) m/z=364, 366 (M+H; 2 bromine isotopes).

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 1111637-74-1, 1-(5-Bromo-2-fluoropyridin-3-yl)ethanone.

Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; CHENG, Yuan; CHOQUETTE, Deborah; EPSTEIN, Oleg; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; HUA, Zihao; HUNGATE, Randall W.; HUMAN, Jason Brooks; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; MINATTI, Ana Elena; OLIVIERI, Philip; ROMERO, Karina; RUMFELT, Shannon; RZASA, Robert M.; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; XUE, Qiufen; ZHENG, Xiao; ZHONG, Wenge; US2014/107109; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 69422-72-6, 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.69422-72-6, name is 2,4,6-Trichloronicotinic acid, molecular formula is C6H2Cl3NO2, molecular weight is 226.4446, as common compound, the synthetic route is as follows.

To 1.7 (1.0 g, 4.42 mmol, 1.0 eq) was added SOCl2(5.0 mL) followed by DMF (catalytic) and reflux ed for 16 h. Reaction mixture was concentrated under reduced pressure to obtain acyl chloride. Methyl hydrazine (0.20 g, 42.5 mmol, 1.0 eq) was dissolved in CH2C12(20.0 mL) followed by addition of solution of NaOH (0.72 g, 177 mmol, 4.0 eq) in water (5.0 mL). To the solution was added previously made acyl chloride solution in CH2C12(20.0 mL) dropwise. Reaction mixture was refluxed for 15 min. After completion of reaction, reaction mixture was transferred into water and extracted with CH2C12. Organic layers were combined, washed with brine, dried over Na2S04and concentrated under reduced pressure to pressure to obtain crude which was purified by column chromatography to provide 1.8. (1.1 g, 97.0 %). MS(ES): m/z 255.5 [M+H]+

The chemical industry reduces the impact on the environment during synthesis 69422-72-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NIMBUS LAKSHMI, INC.; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine C.; LEIT DE MORADEI, Silvana Marcel; MASSE, Craig E.; MCLEAN, Thomas H.; MONDAL, Sayan; (401 pag.)WO2018/71794; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem