Tag: M.W:100-200

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.105250-16-6, name is (2-Methylpyridin-4-yl)methanol, molecular formula is C7H9NO, molecular weight is 123.15, as common compound, the synthetic route is as follows.category: pyridine-derivatives

Example S4: Preparation of 4- (2-Methyl-pyridin-4-yl)-2H-pyrazol-3-ylamine; a) To a stirred mixture of 4-hydroxymethyl-2-methyl-pyridine [CAS No. 105250-16-6] (3.37 g, 27.4 mmol), potassium cyanide (3.56 g, 54.7 mmol) and 18-crown-6 (0.72 g, 2.74 mmol) in acetonitrile (75 ml) was added dropwise at 15-20C a solution of tributylphosphine (7.16 g, 30.1 mmol) in acetonitrile (25 ml). The reaction mixture was stirred at room temperature for 25 h, poured into water (100 ml) and extracted with ethyl acetate (3 x 100 ml). The combined organic layers were washed with water (3 x 100 ml), brine (100 ml) dried (MgSO4) and evaporated. The crude product was further purified by column chromatography on silica gel (ethyl acetate) to yield 4-cyanomethyl- 2-methyl-pyridine (2.26 g, 62%) as a brown oil

At the same time, in my other blogs, there are other synthetic methods of this type of compound,105250-16-6, (2-Methylpyridin-4-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-ROCHE AG; WO2005/40171; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.113118-81-3, name is 5-Bromonicotinaldehyde, molecular formula is C6H4BrNO, molecular weight is 186.0061, as common compound, the synthetic route is as follows.Computed Properties of C6H4BrNO

Intermediate 22(E)-3-Bromo-5-(3-methoxystyryl)pyridine. To a solution of diethyl 3- methoxybenzylphosphonate (5 g, 19.36 mmol) in dimethylformamide (50 mL) at room temperature was added sodium methoxide (2.092 g, 38.7 mmol) and 18-Crown- 6 (2.047 g, 7.74 mmol). After stirring at room temperature for 5 min, the reaction was cooled to 0C and treated with 5-bromonicotinaldehyde (4.32 g, 23.23 mmol) as a solid in one portion. The ice bath was removed and the reaction stirred at room temperature for 2 h. The reaction was poured into water (500 mL) with vigorous stirring. The resulting suspension was extracted with diethyl ether, washed with water (3X), then brine, dried over magnesium sulfate, and concentrated to an oil which crystallized upon standing. The solid was triturated with a minimum of ethanol (ca. 12 mL) and placed in the freezer for 72 h. The resulting solid was broken up with a spatula, collected by filtration, and rinsed with a minimum of cold ethanol to give 3.79 g (68%) as a white crystalline solid. ¾-NMR (CDC13> 500MHz) delta 8.64 (d, J=1.8, IH), 8.57 (d, J=2.1, IH), 8.00 (dd, J=2.1, 1.8, IH), 7.33 (dd, J=7.9, 7.9, IH), 7.10-7.20 (m, 2H), 7.07 (m, IH), 7.01 (d, J=16.5, IH), 6.91 (dd, J=7.6, 2.1, IH), 3.88 (s, 3H). 13C-NMR (CDC13, 126 MHz) delta 160.1, 149.5, 146.7, 137.7, 135.1, 134.8, 132.4, 130.0, 123.7, 121.1, 1 19.6, 1 14.4, 112.2, 55.4. Mass spec: 290.14 (MH)+..

At the same time, in my other blogs, there are other synthetic methods of this type of compound,113118-81-3, 5-Bromonicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DEGNAN, Andrew P.; HUANG, Hong; SNYDER, Lawrence B.; YANG, Fukang; GILLMAN, Kevin W.; PARKER, Michael F.; WO2012/64603; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17288-35-6 ,Some common heterocyclic compound, 17288-35-6, 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.

A mixture of 1H-pyrrolo [3 ,2-bj pyridine15 2-carboxylic acid (69 mg, 426 imol, 1 eq), HATU (162 mg, 426 imol, 1 eq), TEA (86 mg, 851 imol, 119 tL, 2 eq) in 2 mL of DMF was stirred at 15C for 0.5 hour, then compound 30(110 mg, 426 imol, 1 eq, HC1 salt) was added at 15C and the mixture was stirred at 15C for 11.5 hours. The mixture was filtered and the filtrate was purified by prep-HPLC (TFA condition) to give 53.5 mg of compound 418 (98 imol, 23% yield, 95.0% purity, TFA salt) as a brown solid. ?H NMR (400MHz, METHANOL-c/4) oe = 8.67 (d, J=5.6 Hz, 1H), 8.62 (d, J=8.3 Hz, 1H), 7.78(dd, J5.7, 8.3 Hz, 1H), 7.69 – 7.27 (m, SH), 7.22 – 6.90 (m, 1H), 3.90 (br s, 1H), 3.66 – 3.48(m, 2H), 3.07 – 2.76 (m, 1H), 2.38 – 2.03 (m, 2H), 2.01 – 1.67 (m, 4H), 1.44 (br t, J=3.7 Hz,2H), 1.42-1.30 (m, 4H), 1.27 (brt,J=7.OHz, 2H), 1.29- 1.24(m, 1H)LCMS (ESI+): m/z 403.3 (M+H)

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. 17288-35-6, 1H-Pyrrolo[3,2-b]pyridine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AQUINNAH PHARMACEUTICALS, INC.; BURNETT, Duane, A.; VACCA, Joseph, P.; (310 pag.)WO2018/119395; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1101120-37-9, 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.1101120-37-9, name is Pyrazolo[1,5-a]pyridin-5-amine, molecular formula is C7H7N3, molecular weight is 133.15, as common compound, the synthetic route is as follows.

Decarboxylation of ester 3l (1.29 g, 2.98 mmol), except with carrying out the aqueous extraction from pH 12, gave pyrazolo[1,5-a]pyridin-5-amine (7l) as a pale brown solid (310 mg, 78%). 1H NMR delta (400 MHz, CDCl3) 8.23 (d, J = 7.4 Hz, 1H), 7.79 (d, J = 2.0 Hz, 1H), 6.58 (d, J = 2.4 Hz, 1H), 6.22 (dd, J = 7.4, 2.4 Hz, 1H), 6.13 (d, J = 2.0 Hz, 1H), 3.81 (s, 2H). LC-MS (APCI+) 134 (MH+, 100%). A solution of NaNO2 (27 mg, 0.39 mmol) in water (1 mL) was added dropwise to a solution of 7l (40 mg, 0.30 mmol) and CuCl (74 mg, 0.75 mmol) in concentrated HCl (1 mL) at 0 C over 2 min. After 30 min, the reaction mixture was heated to 80 C for 15 min, and then cooled to room temperature, basified to pH 10 with 1 M NaOH, filtered through a plug of celite and washed with CH2Cl2. The layers of the filtrate were separated and the aqueous layer extracted with CH2Cl2. The combined extracts were dried (Na2SO4) and the solvent removed in vacuo. Chromatography (eluting with hexanes: EtOAc 3:1) gave 5-chloropyrazolo[1,5-a]pyridine (7o) as a white solid (6 mg, 13%). 1H NMR delta (400 MHz, CDCl3) 8.38 (d, J = 7.4 Hz, 1H), 7.95 (d, J = 2.2 Hz, 1H), 7.53 (d, J = 1.8 Hz, 1H), 6.71 (dd, J = 7.4, 2.2 Hz, 1H), 6.47 (d, J = 1.8 Hz, 1H). LC-MS (APCI+) 153 (MH+ with 35Cl, 100%), 155 (MH+ with 37Cl, 30%). Vilsmeier reaction of 7o (6 mg, 0.039 mmol) gave 4o as a white solid (7 mg, 100%).

Statistics shows that 1101120-37-9 is playing an increasingly important role. we look forward to future research findings about Pyrazolo[1,5-a]pyridin-5-amine.

Reference:
Article; Kendall, Jackie D.; O’Connor, Patrick D.; Marshall, Andrew J.; Frederick, Raphael; Marshall, Elaine S.; Lill, Claire L.; Lee, Woo-Jeong; Kolekar, Sharada; Chao, Mindy; Malik, Alisha; Yu, Shuqiao; Chaussade, Claire; Buchanan, Christina; Rewcastle, Gordon W.; Baguley, Bruce C.; Flanagan, Jack U.; Jamieson, Stephen M.F.; Denny, William A.; Shepherd, Peter R.; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 69 – 85;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 59576-26-0, 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 59576-26-0, name is 1-(4-Methylpyridin-2-yl)ethanone. This compound has unique chemical properties. The synthetic route is as follows.

Step 1: In a high pressure vial charged with a solution of 1-(4-methylpyridin-2-yl)ethanone (1.0 equiv.) and EtOH (0.1 equiv) in DCM (2.0M) was added DAST (2.5 equiv.). The reaction was heated to 30 oC and heated for 48 hrs. LCMS analysis indicated the formation of the desired product (MH+?157.9, Rt?0.54 min). The reaction was diluted with DCM and quenched with NaHCO3, slowly at 0oC. The phases were separated and the aqueous layer was washed with DCM (2×). The combined organics were dried over MgSO4, filtered, and concentrated. The crude material was purified via flash chromatography over silica gel eluting with heptanes and 0-100percent ethyl acetate gradient. Isolated 2-(1,1-difluoroethyl)-4-methylpyridine in 27percent yield. LCMS (m/z) (M+H)=157.9, Rt=0.54.

According to the analysis of related databases, 59576-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; Barsanti, Paul A.; Burger, Matthew; Lou, Yan; Nishiguchi, Gisele; Polyakov, Valery; Ramurthy, Savithri; Rico, Alice; Setti, Lina; Smith, Aaron; Taft, Benjamin; Tanner, Huw; DiPesa, Alan; Yusuff, Naeem; US2014/275003; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 609-71-2, Adding some certain compound to certain chemical reactions, such as: 609-71-2, name is 2-Oxo-1,2-dihydropyridine-3-carboxylic acid,molecular formula is C6H5NO3, 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 609-71-2.

A stirred suspension of NaH 60% dispersion in mineral oil (206 mg, 5.14 mmol), washed twice with distilled n-hexane and once with Et20 in 2 mL of anhydrous DMF under N2 atmosphere was treated dropwise with a solution containing the 2-hydroxynicotinic acid (600 mg, 4.31 mmol) in 5 mL of anhydrous DMF. The mixture was left under stirring at room temperature for 2h and then 3,4-difluoro-benzylbromide (1.06 g, 5.14 mmol) was added and the mixture stirred and heated at 50C for 1 6h. After the mixture was concentrated under reduced pressure and the residue was treated with water to give a solid, which was collected by vacuum filtration. Next the solid was refluxed for 4h in aq. 10% NaOH (10 mL) and the resulting mixture was cooled and made acid with 1 N aq.HCI. The white solid formed was collected by filtration and washed with nhexane and Et20, giving the derivative 3.9 as white solid (857 mg, 3.23 mmol, 75% yield).1HNMR (400 MHz, DMSO-d6): 65.30 (5, 2H, CH2); 6.78 (t, 1H, J = 6.9 Hz, Ar);7.22-7.24 (m, 1H, Ar); 7.41 -7.53 (m, 2H, Ar); 8.41 (d, 2H, J = 6.9 Hz, Ar) ppm.Anal. Calcd for C13H9NO3F2: C, 58,87%; H, 3.42%; N, 5.28%; Found: C, 58,99%; H, 3.47%; N, 5.43%

According to the analysis of related databases, 609-71-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INTERNATIONAL SOCIETY FOR DRUG DEVELOPMENT S.R.L.; SESTITO, Simona; DANIELE, Simona; MARTINI, Claudia; RAPPOSELLI, Simona; PURICELLI, Guido; (63 pag.)WO2016/198597; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 31181-79-0, (3-Fluoropyrid-2-yl)methanol, 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, Product Details of 31181-79-0, blongs to pyridine-derivatives compound. Product Details of 31181-79-0

Preparation 60; 2-Chloromethyl-3-fluoro-pyridine EPO Dissolve (3-fluoro-pyridin-2-yl)-methanol (215 mg, 1.69 mmol) in dichloromethane (10 mL) and cool to 0 0C. Add thionyl chloride (160 muL, 2.20 mmol) and stir the reaction for one hour. Add dichloromethane (50 mL) and stir the reaction with saturated aqueous sodium bicarbonate (2 x 40 mL) and brine (2 x 40 mL). Separate and dry the organic portion over magnesium sulfate, filter, and concentrate under reduced pressure to provide 198 mg (80%) of product, which is used without further purification. MS: m/z 146, 148 [C6H5ClFN + I]+; 1H NMR (300 MHz, CDCl3): delta 8.41-8.44 (m, IH), 7.41-7.47 (m, IH), 7.28-7.34 (m, IH), 4.75 (d, J = 2.0 Hz, 2H); 19F NMR (282 MHz, CDCl3): delta -123.8.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,31181-79-0, (3-Fluoropyrid-2-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/2181; (2007); 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 70298-88-3, name is 2,2-Dimehtyl-N-pyridin-3-yl-propionamide. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

In the three bottle,3-Pivalamidopyridine (20.0 g, 112.2 mmol) was dissolved in anhydrous tetrahydrofuran (200 mL).In nitrogen protection, the temperature drops to -78 C,N-butyllithium (17.8 g, 280.5 mmol) was added dropwise and the solution was dropped.Slowly warming to 0C for 3 hours,Then cool down to -78 C,N-methyl-N-methoxyacetamide (17.4 g, 168.3 mmol) was added dropwise.After completion of the dropwise addition, the reaction was slowly warmed to room temperature for 10 h.After the reaction was completed, the reaction was quenched with 1N hydrochloric acid, extracted with ethyl acetate (100 mL×3), and the organic phase was collected and washed with saturated brine (100 mL×1).The solvent was evaporated under reduced pressure to give crude N-(4-ethanhydrin-3-yl)trimethylacetamide.The crude product was applied on a silica gel column (mobile phase: PE_EA=5:1) to obtain 11.2 g of a pure product with a yield of 45.4%.

With the rapid development of chemical substances, we look forward to future research findings about 70298-88-3.

Reference:
Patent; Guizhou University; Liu Li; Huang Zhuyan; Yue Yi; (8 pag.)CN107382839; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1513-66-2, 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 1513-66-2, name is 2,3-Difluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step 18 A mixture of A17 (60 mg, 0.10 mmol), 2,3 -difluoropyri dine (24 mg, 0.21 mmol) and Cs2C03 (101 mg, 0.308 mmol) in DMSO (1 mL) was stirred at 65C for 2 h. The mixture was diluted with water (30 mL) and extracted with EtOAc (3 x 25 mL). The combined organic layers were dried over Na2S04 and filtered to afford the crude product of A18, which was used in the next step directly without further purification.

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 1513-66-2, 2,3-Difluoropyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn, P.; CUMMING, Jared, N.; DAI, Xing; (84 pag.)WO2017/139210; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.1060811-62-2, name is 4,6-Dichloronicotinaldehyde, molecular formula is C6H3Cl2NO, molecular weight is 176, as common compound, the synthetic route is as follows.Formula: C6H3Cl2NO

A pre-mixed stirred solution of compound 3 (7.4 g, 42.28 mmol) in dichloromethane (40 mL) containing triethyl amine (11.37 mL, 84.56 mmol) was added ethyl mercaptoacetate (5.59 mL, 50.74 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 1 h and then to 50 °C for 18 h. The reaction mixture was quenched with water and extracted with ethyl acetate. After usual standard work up procedure and purification by column chromatography (silica gel: 100-200 mesh, eluent: 5percent ethyl acetate in pet ether) isolated compound 4; Light Yellow solid; Yield: 5.7 g, 56 percent; m.p.: 108-112 °C. Elemental analysis of C10H8NO2SCl calcd. (found) percent: C 49.69 (49.71), H 3.34 (3.32), N 5.80 (5.77)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1060811-62-2, 4,6-Dichloronicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Article; Sree Lakshmana Rao; Basaveswara Rao, Mandava V.; Prasad; Asian Journal of Chemistry; vol. 31; 3; (2019); p. 627 – 632;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem