Category: 105752-11-2

Application of 105752-11-2, 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.105752-11-2, name is 3-Amino-4-iodopyridine, molecular formula is C5H5IN2, molecular weight is 220.0111, as common compound, the synthetic route is as follows.

2,6-dichloro-[3,4′-bipyridin]-3′-amine (i64): To a stirred solution of 4-iodopyridin-3-amine (2 g, 9.0 mmol) in 1 ,4-dioxane (84 ml_), (2,6- dichloropyridin-3-yl) boronic acid (2.4 g, 12.5 mmol) and K3P04 (5.6 g, 26.0 mmol) solution in water (28 mL) were added and the reaction was degassed with argon for 20 min. PdCI2(PPh3)2 (0.7 g, 0.99 mmol) was added and the reaction was heated in a sealed tube at 100C for 16 h. The progress of the reaction was monitored by TLC. After completion, the reaction was diluted with water and filtered. The aqueous layer was extracted with ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude product was purified by silica gel (100:200 mesh) column chromatography using 2% methanol in dichloromethane as eluent to afford 2,6-dichloro-[3,4′-bipyridin]-3′-amine (64) (1 .08 g, Yield 51 %). 1 H NMR (400 MHz, DMSO-d6) delta 5.26 (s, 2H), 6.93 (d, J = 4.9 Hz, 1 H), 7.51 -7.68 (m, 1 H), 7.79- 7.89 (m, 2H), 8.08 (s, 1 H), MS (ESI) m/e (M+1 )+: 240.00

Statistics shows that 105752-11-2 is playing an increasingly important role. we look forward to future research findings about 3-Amino-4-iodopyridine.

Reference:
Patent; UCB BIOPHARMA SPRL; MERCIER, Joel; PROVINS, Laurent; VERMEIREN, Celine; SABNIS, Yogesh Anil; (106 pag.)WO2016/124508; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 105752-11-2, 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 105752-11-2, name is 3-Amino-4-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows.

A reselable pressure tube was charged with 4-iodopyridin-3 -amine (2.4 g, 10.9 mmol), 4-(triethylsilyl)but-3-yn-ol (5.0 g, 27.3 mmol), lithium chloride (0.46 g, 42.0 mmol), sodium carbonate (2.31 g, 21.8 mmol) and 1,1 ‘- bis(diphenylphosphino)ferrocenopalladium(II) dichloride, toluene (0.45 g, 0.55 mmol), the tube was sealed and heated on a 100 C oil bath for ~20h. The reaction mixture was cooled to ambient temperature, diluted with EtOAc (75 mL) and ether (75 mL). Water (150 mL) was added and the biphasic mixture was filtered through celite. The filtrate was transferred to a separatory funnel and the phases were separated and the aqueous fraction extracted twice more with ethyl acetate. The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and evaporated. The crude was purified by silica gel chromatography, eluting with 2-20% (9: 1 MeOH/NH4OH)/chloroform, affording 2- (2-(triethylsilyl)-lH-pyrrolo[2,3-c]pyridin-3-yl)ethanol (2.45 g, 81% yield). LCMS method A: retention time = 3.44 min, M+H = 277.25. 1H NMR (400MHz, CHLOROFORM-d) delta = 8.79 (s, 1H), 8.65 – 8.47 (m, 1H), 8.22 (d, J=5.5 Hz, 1H), 7.56 (d, J=5.3 Hz, 1H), 3.91 (t, J=6.9 Hz, 2H), 3.13 (t, J=6.9 Hz, 2H), 1.82 (br. s, 1H), 1.12 – 0.90 (m, 15H).

According to the analysis of related databases, 105752-11-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MCDONALD, Ivar M.; ZUSI, F. Christopher; OLSON, Richard E.; WO2015/191403; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 105752-11-2, 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. 105752-11-2, name is 3-Amino-4-iodopyridine. A new synthetic method of this compound is introduced below.

A dry, 50 mL, one neck round bottom flask was charged with freshly sublimed 3-amino-4-iodopyridine (1.17 g, 5.32 mmol, Alfa Aesar), A-Phos (565 mg, 0.80 mmol), and a stirbar in a glove box. The flask was sealed with a septa, and moved to a standard fume hood. The septa was pierced with an Ar inlet, and the solids were treated with a 0.61 M THF solution of (3,5- dimethylisoxazol-4-yl)zinc(II) iodide (3.83 g, 13.29 mmol), The reaction was stirred at RT for 48 h. The reaction was carefully poured onto an aqueous 0.54 M EDTA, pH adjusted to 7.6 with LiOH (29.5 ml, 15.95 mmol, MP Biomedicals) solution. The transfer was quantitated with dry THF (3 x 20 mL). The mixture was stirred for 1 h, and the bulk of organic solvent was removed using a rotary evaporator. The aqueous mixture was extracted with 1% l,l,l,3,3,3-hexafluoro-2-propanol in CHCI3 (4 x 60 mL) and each extract was sequentially passed through an unbuffered Varian Chem Elut (CEIOIO). The total elution volume was concentrated in vacuo. The residue was transferred to a 100 mL round bottom flask, and treated with SiliaMetS TAAcOH (0.49 mmol/g loading, 10.85 g, 5.32 mmol, Silicycle). The flask was then charged with dry THF (40 mL), and a stirbar. The flask was fitted with a reflux condenser/ Ar inlet and heated at 70 C for 1 h. The solution was cooled over a 30 minute period, and the solvent was removed in vacuo. The powder was further dried at reduced pressure overnight (final pressure = 0.10 mm Hg). The silica was loaded onto a silica gel column and the crude material was purified by silica gel chromatography (10% EtOH in DCE). The crude material was treated wtih acetone (5 mL), and stirred in an ice-water bath. The slurry was N2-pressure filtered through a glass frit (10 mL Bohdan) fitted with a 0.22 muiotaeta PTFE, 25 mm syringe filter unit (Millipore, SLFG025NK). The solids were washed with cold acetone (3 x 2 mL) and discarded. The solvent was removed under reduced pressure, and the oily residue was dried at RT and 0.1 mm Hg vacuum for 2 h to afford 4-(3,5-dimethylisoxazol-4- yl)pyridin-3-amine (1.15 g, 6.08 mmol, 114 % yield). MS (ESI, pos. ion) m/z: 190.1 (M+l).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,105752-11-2, 3-Amino-4-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; D’AMICO, Derin C.; HERBERICH, Bradley J.; JACKSON, Claire L.M.; PETTUS, Liping H.; TASKER, Andrew; WANG, Hui-Ling; WU, Bin; WURZ, Ryan; WO2012/148775; (2012); 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.105752-11-2, name is 3-Amino-4-iodopyridine, molecular formula is C5H5IN2, molecular weight is 220.0111, as common compound, the synthetic route is as follows.Formula: C5H5IN2

To a mixture of 4-iodopyridin-3-amine (40 g, 182 mmol) and ethyl acrylate (27 g, 272 mmol) in DMF (300 mL), DIPEA (28 g, 218 mmol) was added. Then Pd(OAc)2 (4 g, 18 mmol) and P(o-tol)3 (11 g, 36 mmol) were added quickly under N2 atmosphere. The mixture was stirred at 85 C for 12 h under N2 atmosphere. After cooling down, the solvent was removed under reduced pressure. The residue was purified by silica gel column (DCM/ MeOH = 20/1) to give ethyl (E)-3-(3-aminopyridin-4-yl)acrylate (20 g, yield: 57%) as a yellow oil. ESI-MS (M+H): 193.1. ?H NMR (400 MHz, CDC13) (5: 8.15 (s, 1H), 8.02-7.98 (m, 1H), 7.72 (d, J= 16.4 Hz, 1H), 7.18 (d, J= 5.2 Hz, 1H), 6.48 (d, J= 16Hz, 1H), 4.27 (q, J= 7.2 Hz, 2H), 4.07 (s, 2H), 1.34 (t, J= 7.2Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,105752-11-2, 3-Amino-4-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; BIOGEN MA INC.; CAPACCI, Andrew, George; DECHANTSREITER, Michael; ENYEDY, Istvan; JONES, John, H.; LIN, Edward, Yin-Shiang; LUCAS, Brian, Stuart; MA, Bin; (273 pag.)WO2018/140876; (2018); 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.105752-11-2, name is 3-Amino-4-iodopyridine, molecular formula is C5H5IN2, molecular weight is 220.0111, as common compound, the synthetic route is as follows.name: 3-Amino-4-iodopyridine

Step 1: 4-[(2-fluorophenyl)ethvnyl]pyridin-3-amineTo a solution of 3-amino-4-iodopyridine in Dioxane/DMF (1 :1, 0.7M) were sequentially added NEt3 (5eq.), CuI (0.04 eq.), trans-bis(triphenylphosphine) palladium(II) chloride (0.02 eq.) and l-ethynyl-2-fluorobenzene (2 eq.). After heating for 1 h at 70 0C, water was added and the mixture was extracted with Et2O. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel, eluting with PE/EtOAc (50:50), affording the title compound(80%) as a solid. 1H NMR (400 MHz, OMSO-d6 + TFA, 300K) delta, 7.26-7.33 (dd, 2H, J = 7.6 Hz, J= 8 Hz), 7.52-7.53 (m, IH), 7.78 (d, IH, J= 8 Hz), 7.83 (t, IH, J= 6.4 Hz), 7.7 (d, IH, J= 5.6 Hz), 8.21 (s, IH); MS (ES+) m/z 213 (M +H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,105752-11-2, 3-Amino-4-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.P.A.; NARJES, Frank; HABERMANN, Jorg; COLARUSSO, Stefania; WO2010/115901; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 105752-11-2, 3-Amino-4-iodopyridine, 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, Application In Synthesis of 3-Amino-4-iodopyridine, blongs to pyridine-derivatives compound. Application In Synthesis of 3-Amino-4-iodopyridine

To a stirred solution of 4-iodopyridin-3-amine (500 mg, 2.2 mmol) in acetonitrile (5 mL) wasadded tert-butyl (2-amino-2-thioethoxyethyl)carbamate (561 mg, 2.9 mmol) and CaO (255 mg,4.5 mmol) at room temperature. The reaction mixture was purged with argon for 15 minutes,then dppf (151 mg, 0.27 mmol) and Pd2(dba)3 (64 mg, 0.06 mmol) was added to the reactionmixture. The reaction mixture was purged with argon for further 5 minutes and stirred in sealedtube at 60 C for 16 h. The reaction mixture was filtered through celite pad and washed the pad

At the same time, in my other blogs, there are other synthetic methods of this type of compound,105752-11-2, 3-Amino-4-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; ANTABIO SAS; LEIRIS, Simon; DAVIES, David Thomas; EVERETT, Martin; SPRYNSKI, Nicolas; SUTTON, Jonathan Mark; BODNARCHUK, Michael Steven; PALLIN, Thomas David; CRIDLAND, Andrew Peter; BLENCH, Toby Jonathan; CLARK, David Edward; ELLIOTT, Richard Leonard; (197 pag.)WO2018/172423; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 105752-11-2, 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.105752-11-2, name is 3-Amino-4-iodopyridine, molecular formula is C5H5IN2, molecular weight is 220.0111, as common compound, the synthetic route is as follows.

A 10 mL CEM microwave vessel was charged with 3-amino-4-iodopyridine (139 mg, 0.63 mmol, Alfa Aesar), 3,6-dihydro-2H-pyridine-l-A^-boc-4-boronic acid pinacol ester (236 mg, 0.76 mmol, Frontier Scientific Inc.), NaOAc (155 mg, 1.90 mmol) and a stirbar. The vessel was sealed, and transferred into a glove box using a standard antichamber evacuate-refill cycle (3 times). The vessel was charged with A-Phos (45 mg, 0.063 mmol, Sigma-Aldrich), and sealed. The vessel was then transferred to a standard hood, and treated with dioxane (4 mL), and water (0.4 mL). The slurry was sonicated and was then heated in a microwave using a CEM explorer at 120 C for 30 min. The solution was treated with a second aliquat of 3,6-dihydro-2H-pyridine-l-A x>c-4-boronic acid pinacol ester (236 mg, 0.76 mmol, Frontier Scientific Inc.) and was then heated in a microwave using a CEM explorer at 120 C for 30 min The solution was treated with dichlorobis(di-?er?-butylphenylphosphine)palladium(II) (20 mg, 0.032 mmol, Alfa Aesar) and was then heated in a microwave using a CEM explorer at 120 C for 30 min. The solution was cooled to RT overnight under a stream of N2. The residue was treated with dry THF (5 mL) and SiliaMetS TAAcOH (1.29 g, 0.63 mmol, Silicycle). The vessel was crimped with a PTFE lined seal, and heated at 60 C for 3 h. The slurry was N2- pressure filtered through a glass frit (10 mL Bohdan) fitted with a 0.22 muiotaeta PTFE, 25 mm syringe filter unit (Millipore, SLFG025NK). The silica was washed with dry THF (5 x 5 mL), and concentrated in vacuo. The crude material was purified by silica gel chromatography (10% EtOH in DCE) to afford teri-butyl 3′-amino-5,6-dihydro-[4,4′- bipyridine]-l(2H)-carboxylate (77 mg, 0.28 mmol, 44 % yield). MS (ESI, pos. ion) m/z: 276.0 (M+l).

Statistics shows that 105752-11-2 is playing an increasingly important role. we look forward to future research findings about 3-Amino-4-iodopyridine.

Reference:
Patent; AMGEN INC.; D’AMICO, Derin C.; HERBERICH, Bradley J.; JACKSON, Claire L.M.; PETTUS, Liping H.; TASKER, Andrew; WANG, Hui-Ling; WU, Bin; WURZ, Ryan; WO2012/148775; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem