Tag: M.W:200-300

Electric Literature of 57883-25-7, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 57883-25-7 as follows.

A suspension of 3-bromo-2-ethoxypyridine (Preparation 1 1 , 28.69 g, 142.0 mmol), bis(pinacolato)diboron (43.3 g, 170.5 mmol), and potassium acetate (41 .8 g, 425.9 mmol) in DMSO (100 mL) was degassed with nitrogen and [1 ,1 ‘- bis(diphenylphosphinoferrocene]dichloro palladium (II) (5.8 g, 7.93 mmol) was added and the reaction mixture was stirred for 6 hours at 95 C. The reaction mixture was filtered through a pad of Arbocel which was washed with ethyl acetate (500 mL). The filtrate was concentrated in vacuo and the crude material was purified by silica gel column chromatography eluting with 50% ethyl acetate in cyclohexane to afford the title compound as a red oil (34.4g, 74%). 1H NMR (400MHz, CDCl3): delta ppm 1 .35 (s, 12H), 1 .39 (m, 3H), 4.37 (m, 2H), 6.81 (m, 1 H), 7.89 (m, 1 H), 8.19 (m, 1 H). LCMS Rt = 3.27 minutes MS m/z 250 [MH]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,57883-25-7, its application will become more common.

Reference:
Patent; PFIZER LIMITED; STORER, Robert, Ian; SWAIN, Nigel, Alan; WO2013/93688; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 639091-75-1, Adding some certain compound to certain chemical reactions, such as: 639091-75-1, name is Methyl 2-(Boc-amino)isonicotinate,molecular formula is C12H16N2O4, 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 639091-75-1.

A 500mL round bottomed flask was charged with methyl 2-((tert-butoxycarbonyl)amino)isonicotinate (5.95 g, 23.6 mmol) and suspended in methanol (1 18 ml). To this stirring solution was added 3.0M potassium hydroxide (23.6 mL, 70.8 mmol). The flask was vented and heated to 50 C for 10 minutes. LCMS analysis showed clean and complete conversion of starting material to a single product consistent with the desired product by mass (m/z=237[M-H]-). The mixture was cooled to room temperature and then 1.ON HCl was added to give a white precipitate. The solid was collected by filtration and dried overnight to give 2-((tert- butoxycarbonyl)amino)isonicotinic acid, HCl (5.2 g, 18.93 mmol, 80 % yield). 1H NMR (400 MHz, DMSO-d6) delta ppm 13.64 (1 H, br. s.), 10.06 (1 H, s), 8.39 (1 H, d, J=5.27 Hz), 8.30 (1 H, s), 7.42 (1 H, dd, J=5.02, 1.51 Hz), 1.48 (9 H, s).

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. 639091-75-1, Methyl 2-(Boc-amino)isonicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SCHMITZ, William D.; DEBENEDETTO, Mikkel V.; KIMURA, S. Roy; WO2013/3298; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1062368-71-1 ,Some common heterocyclic compound, 1062368-71-1, molecular formula is C9H7BrN2O2, 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.

Methyl 4-bromopyrazolo [1,5 -a]pyridine-3 -carboxylate (100 mg, 0.39 mmol), Pd(OAc)2 (5.3 mg, 0.024 mmol), BNAP (22 mg, 0.035 mmol) and Cs2CO3 (192 mg, 0.59 mmol) were placed in a pressure vial. The reaction mixture was degassed (3x vacuum and argon), then toluene (2 mL) and morpholine (0.044 mL, 0.51 mmol) were added. Thereaction mixture was degassed again, and then was stirred at 120 C for 3 h. After cooled to rt, the reaction was filtered through a pad of CELITE, and the solvent was removed. The crude product was purified by reverse phase chromatography to provide Intermediate 109 (74 mg, 72%) as a light tan solid. ?H NMR (400MHz, CDC13) oe 8.46 (s, 1H), 8.43 (d, J=6.6 Hz, 1H), 7.31 (d, J=7.7 Hz, 1H), 7.05 (t, J7.2 Hz, 1H), 4.11 – 4.04(m, 4H), 3.94 (s, 3H), 3.40 – 3.27 (m, 4H). LC-MS(ESI) m/z: 262.0 [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,1062368-71-1, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LADZIATA, Vladimir; GLUNZ, Peter W.; HU, Zilun; WANG, Yufeng; (0 pag.)WO2016/10950; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17117-13-4, Adding some certain compound to certain chemical reactions, such as: 17117-13-4, name is 2-Bromo-4-ethoxypyridine,molecular formula is C7H8BrNO, 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 17117-13-4.

Preparation 36 To a suspension of 2-bromo-4-ethoxypyridine (879 mg), 3-nitrophenylboronic acid (944 mg) and tetrakis(triphenylphosphine)-palladium (251 mg) in 1,2-dimethoxyethane (20 ml) was added 2M aqueous solution of sodium carbonate (5.66 ml). The mixture was stirred at 90 C. for 8 hours under a nitrogen atmosphere, then cooled to room temperature and diluted with ethyl acetate. The organic layer was separated, washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 40 g, 25% ethyl acetate in n-hexane) to give 3-(4-ethoxypyridin-2-yl)nitrobenzene (887 mg). 1H-NMR (CDCl3): delta1.49(3H,t,J=7.0 Hz), 4.18(2H,q,J=7.0 Hz), 6.83(1H,dd,J=5.7 Hz,2.4 Hz), 7.29(1H,d,J=2.4 Hz), 7.63(1H,t,J=8.0 Hz), 8.2-8.4(2H,m), 8.54(1H,d,J=5.7 Hz), 8.81(1H,t,J=2.0 Hz)

According to the analysis of related databases, 17117-13-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US6521643; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 885275-59-2 , The common heterocyclic compound, 885275-59-2, name is 6-Chloro-3-iodoimidazo[1,2-a]pyridine, molecular formula is C7H4ClIN2, 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 A-3 (1.00 g, 3.59 mmol), Cul (3.42 g, 17.95 mmol), TMSCF3 (1.53 g, 10.77 mmol) and KF (625.90 mg, 10.77 mmol, 252.38 mu,) in DMF (40.00 mL) was stirred at 95 C for 2 hours under N2, at which point the desired product was observed by LCMS. The mixture was then quenched with 0 (100 mL) and extracted with EtOAc (200 mL x 2). The combined organic layers were washed with 0 (100 mL x 2), brine (100 mL), dried over Na2S04, filtered and concentrated to give the crude product, which was purified by silica gel (PE : EtOAc = 15:1 to EtOAc) to afford A-4 (140.00 mg, 634.69 umol) as a solid. H NMR (CDCI3 400 MHz) delta = 8.28 (s, 1H), 7.98 (d, 1H), 7.69 (d, 1H), 7.37 (dd, lH)..Synthesis of Compound 1: A mixture of A-4 (100.0 mg, 453.35 muiotaetaomicron), [4-(trifluoromethoxy)phenyl]boronic acid (140.04 mg, 680.03 muiotaetaomicron), Pd(i-Bu3P)2 (23.17 mg, 45.34 muiotaetaomicron) and K3P04 (192.47 mg, 906.70 muiotaetaomicron) in dioxane (5.00 mL) and 0 (1.00 mL) was stirred at 80 C for 16 hours under N2. The mixture was then concentrated to give the crude product that was purified by Prep- HPLC to afford Compound 1 (87.14 mg) as a solid. H NMR (400 MHz, CDC13) deltaEta 8.35 (s, 1H), 8.01 (d, 1H), 7.82 (d, 1H), 7.65 – 7.55 (m, 3H), 7.37 (d, 2H). LCMS R, = 1.341 min in 2.0 min chromatography, MS ESI calcd. for [M+H]+ 347.1, found 346.9.

The synthetic route of 885275-59-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRAXIS PRECISION MEDICINES, INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew Mark; MARRON, Brian Edward; (168 pag.)WO2018/98500; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1026201-45-5, Adding some certain compound to certain chemical reactions, such as: 1026201-45-5, name is 8-Bromoimidazo[1,2-a]pyridine-2-carboxylic acid,molecular formula is C8H5BrN2O2, 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 1026201-45-5.

A suspension of intermediate 39 (322 mg, 1.34 mmol) and carbonyldiimidazole (238 mg, 1.47 mmol) in THF (11 ml) was stirred at r.t. for 2 h. DIPEA (0.233 ml, 1.34 mmol) was added and the resulting mixture was stirred for 30 min. at r.t. Then DMF (2 ml) was added to the suspension and the mixture was stirred for 60 h at r.t. The r.m. was cooled to 0 0C and O,N-dimethyl-hydroxylamine (143 mg, 1.47 mmol) was added. The mixture was stirred for 20 h at r.t. The solvents were evaporated under reduced pressure. The residue was dissolved in DCM and washed 3 times with H2O. The organic layer was dried (MgSO4), filtered and evaporated under reduced pressure. The residue was purified via flash column chromatography over silicagel (eluent: DCM/MeOH(NH3) from 100/0 to 99/1). The product fractions were collected and the solvent was evaporated in vacuo. Yield: 216 mg of intermediate 42 (57 %).

According to the analysis of related databases, 1026201-45-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; GIJSEN, Henricus, Jacobus, Maria; MACDONALD, Gregor, James; BISCHOFF, Francois, Paul; TRESADERN, Gary, John; TRABANCO-SUAREZ, Andres, Avelino; VAN BRANDT, Sven, Franciscus, Anna; BERTHELOT, Didier, Jean-Claude; WO2010/70008; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 800401-70-1, Ethyl 5-bromo-1H-pyrrolo-[2,3-c]-pyridine-2-carboxylate, 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, Formula: C10H9BrN2O2, blongs to pyridine-derivatives compound. Formula: C10H9BrN2O2

To a solution OF 5-BROMO-LH-PYRROLO [2,3-c] pyridine-2-carboxylic acid ethyl ester (Preparation 26,0. 160g, 0. 590MMOL) in DMF (anhydrous, 5ML) was added zinc (II) cyanide (0.041g, 0.35mmol) then tetrakis-triphenylphosphine palladium (0). The reaction mixture was degassed by bubbling argon through it for l Omin. The reaction mixture was heated to reflux temperature for 4. 5h then allowed to cool to rt. Water (30mL) was added and the mixture extracted with ethyl acetate (2X50ML). The combined organics were washed with brine (30mL), dried (MGS04), filtered and concentrated in vacuo. The residue was dissolved in ethyl acetate then adsorbed onto silica gel. Purification via flash column chromatography (SI02, ethyl acetate: isohexane, 1: 3, v/v) gave the title compound as a white solid. aH (CDCl3): 1.45 (3H, t), 4.49 (2H, quartet), 7.31 (1H, s), 8.09 (1H, s), 8.97 (1H, s), 9.60 (1H, br s); M/Z (ES+) = 216 [M+ H] + ; RT = 3. 03MIN.

The synthetic route of 800401-70-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OSI PHARMACEUTICALS, INC.; WO2004/104001; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1060814-91-6, Ethyl 2-(4-bromopyridin-2-yl)acetate, 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, Formula: C9H10BrNO2, blongs to pyridine-derivatives compound. Formula: C9H10BrNO2

To a solution of compound 6-7 (2.5 g, 10.24 mmol, 1 eq) and compound 6-10 (2.6 g, 10.24 mmol, 1 eq) in dioxane (40 mL) was added potassium acetate (3.02 g, 30.73 mmol, 3 eq) and Pd(dppf)Cl2.CH2Cl2 (418 mg, 512.12 umol, 0.05 eq). The mixture was degassed under vacuum and purged with nitrogen for three times. The mixture was stirred at 85C for 2 hours under nitrogen atmosphere. TLC (petroleum ether: ether: ethyl acetate = 2:1) showed the starting material was consumed completely and a new spot was formed. The mixture was used directly without work up.

The synthetic route of 1060814-91-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH; TRI-INSTITUTIONAL THERAPEUTICS DISCOVERY INSTITUTE, INC.; FUSHIMI, Makoto; SCALTRITI, Maurizio; HELLER, Daniel, Alan; MONTERRUBIO MARTINEZ, Carles; ARRUABARRENA ARISTORENA, Amaia; MEINKE, Peter, T.; FOLEY, Michael, Andrew; ASANO, Yasutomi; ASO, Kazuyoshi; TAKAHAGI, Hiroki; SHAMAY, Yosef; BASELGA TORRES, Jose, Manuel; SASAKI, Yusuke; MICHINO, Mayako; (271 pag.)WO2020/72892; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 878197-68-3, 5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde, 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, Formula: C8H5BrN2O, blongs to pyridine-derivatives compound. Formula: C8H5BrN2O

The reactor is charged with N-methylpiperazine (3.1 Kg, 31 mol ) and tetrahydrofuran (10 Liters) and stirred under nitrogen while cooling to negative 20 0C. n-Butyl lithium (10.4 L, 26.0 mol) is added to the reaction at a rate to maintain the negative 20 0C temp and the contents are stirred for 15 to 30 minutes. A slurry of 5- bromoimidazo[1 ,2-a]pyridine-2-carbaldehyde (2.79 Kg, 12.4 mol) in tetrahydrofuran (10 Liters) is added at a rate to maintain the reaction at ?0C. The slurry is washed in with additional tetrahydrofuran (6 Liters). The reaction is stirred for 30 minutes and warmed to approximately negative 10 0C. The reaction is quenched by addition of 6N HCI solution to achieve pH 4.0 while maintaining at ? 150C. The reaction is diluted with heptane (14 Liters) and the layers allowed to separate. The lower aqueous layer is drained and the upper organic layer is washed with 1 N HCI (2 x 1.5 Liters). The combined aqueous layers are stirred at 20 degrees and adjusted to pH 9 with 4N NaOH solution. The Aqueous layer is extracted with 10% iPrOH/CH2CI2 (3 x 28 Liters) and the combined organic layers are washed with saturated NaHCO3 solution (14 Liters) and evaporated at <25 0C to approximately 3 volumes, lsopropanol (28 Liters) is added and reaction again concentrated under reduced pressure to approximately 8.5 Liters, lsopropanol (17 Liters) is added and the reaction is treated with a solution of oxalic acid (1.0 Kg, 11.1 mol) in isopropanol (7 Liters) at a rate to maintain good stirring and temperature between approximately 25-4O0C. The reaction is stirred for 30 minutes and the solids are collected and washed with isopropanol (8.5 Liters) Solids are dried at 50 0C to yield 5-(4-methyM- piperazinyl)imidazo[1 ,2-a]pyridine-2-carbaldehyde, (2.25 Kg, 54% yield) 1 H NMR (400 MHz, DMSO-D6) delta ppm 10.01 (s, 1 H) 8.47 (s, 1 H) 7.41 (m, 2 H) 6.65 (m, 1 H) 3.34 (s, 8 H) 2.78 (s, 3 H) At the same time, in my other blogs, there are other synthetic methods of this type of compound,878197-68-3, 5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde, and friends who are interested can also refer to it. Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/26703; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 183208-34-6 , The common heterocyclic compound, 183208-34-6, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridin-2-one, molecular formula is C7H5BrN2O, 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.

In the 250 ml flask is sequentially added in 50 ml ethanol and 5 – bromo -1 – hydrogen pyrrolo [2,3 – the b] pyridine -2 – ketone (4.2g, 20 mmol), Sn powder (4.7 g, 40 mmol) and 5 mol/L hydrochloric acid (14 ml), 40 C stirring for 2 hours, the reaction is completed, to remove the ethanol, add 50 ml of water residue is completely dissolved, saturatedNaHCO3solution and to PH=8, and filtering the resulting solid, after drying, dissolved in 50 ml chloroform, addingCuBr2(13.4 g, 60mmol), 60 Cstirring for 2 hours, the reaction is completed, the end of the reaction, rotary evaporated to remove chloroform, adding 50 ml saturatedNaHCO3solution, ethyl acetate (3 × 100 ml), the combined organic phase with water (50 ml) for washing and then the saturated salt water (50 ml) washing, anhydrousNa2SO4drying, filtering, the filtrate is concentrated to obtain 5 – bromo – 1H – pyrrolo [2,3 – the b] pyridine the crude product, the crude product is chloroform: hexane=2:1 (volume ratio) mixed solution recrystallize to get 3.1 g of pale yellow 5 – bromo – 1H – pyrrolo [2,3 – the b] pyridine pure product, yield 77.6%, melting point:176.8-177.3 C,

The synthetic route of 183208-34-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Heze University; Fan, Hongli; Li, Fenghai; Xu, Meiling; Guo, Qianqian; (7 pag.)CN106045995; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem