Category: 88511-27-7

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.88511-27-7, name is 4-Amino-3-iodopyridine, molecular formula is C5H5IN2, molecular weight is 220.0111, as common compound, the synthetic route is as follows.COA of Formula: C5H5IN2

General procedure: Procedure A : Suzuki coupling To a solution of iodopyridine (1 eq) in dioxane (5 mL/mmol), the boronic acid (1.5 eq), and 1 M Na2C03 aqueous solution (3 eq) were added and the reaction mixture was degassed with argon for 20 min. Then Bis(triphenylphosphine)palladium(ll) dichloride (0.2 eq) was added and the reaction mixture was heated at 100C for 16h. After completion of reaction, the reaction mixture was filtered through a celite pad and the filtrate was concentrated under reduced pressure to afford a residue that was dissolved in water and extracted with ethyl acetate. The organic layer was separated, dried over sodium sulphate and concentrated under reduced pressure to afford the crude product, which was further purified by silica gel (100:200 mesh) column chromatography to afford the Suzuki coupling product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,88511-27-7, 4-Amino-3-iodopyridine, and friends who are interested can also refer to it.

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

Electric Literature of 88511-27-7, Adding some certain compound to certain chemical reactions, such as: 88511-27-7, name is 4-Amino-3-iodopyridine,molecular formula is C5H5IN2, 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 88511-27-7.

General procedure: a suspension of 3-iodo-4-aminopyridine (1 mmol), methyl 2-mercaptoacetate (1.5 equiv), copper (I) iodide (0.05 mmol), trans-N,N’-dimethylcyclohexane-1,2-diamine (0.1 mmol) and cesium carbonate(2 equiv) in dry 1,4-dioxane (4 mL) in a vial was degassed by bubbling N2 into the suspension for 3 min while stirring. The vial was then capped tightly. The mixture was heated at 100 C (oil bath temperature) for 15 h. After coolingto rt, filtration was carried out. The combined filtrates were concentrated on rotavap and the residue was subjected to silica gel column chromatographpurification (5% methanol in methylene chloride) furnishing 3b as a beige solid. 1H NMR (400 MHz, CD3OD) d 8.42 (s, 1H, ArH), 8.26 (s, 1H, ArH), 6.96 (d,J = 5.4 Hz, 1H, ArH), 3.40 (s, 2H, CH2). 13C NMR (400 MHz, CD3OD) d 167.4,148.4, 148.1, 146.0, 29.6.

According to the analysis of related databases, 88511-27-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Huang, Wei-Sheng; Xu, Rongsong; Dodd, Rory; Shakespeare, William C.; Tetrahedron Letters; vol. 54; 38; (2013); p. 5214 – 5216;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 88511-27-7, Adding some certain compound to certain chemical reactions, such as: 88511-27-7, name is 4-Amino-3-iodopyridine,molecular formula is C5H5IN2, 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 88511-27-7.

To a solution of 4-aminopyridine (1a, 37.65 g, 0.4 mole) in HOAc (200 mL) was added iodine monchloride (130 g, 0.8 mole) portionwise. The reaction mixture was stirred at 45 C. for 20 h, then diluted with water (500 mL). The mixture was cooled to 0 C., and basified 30% NaOH to pH=9-10. The solution was extracted with EtOAc (1 L×2) and the combined extracts were washed with 15% Na2S2O3 (400 mL×2), water, brine, dried over Na2SO4, and evaporated in vacuo to give 1b (62 g) as a light yellow solid. ES-MS m/z 221 (MH+). [0185] Into a pressure flask was added 1b (4.4 g, 20 mmol), cupric iodide (228 mg, 1.2 mmol), (trimethylsilyl)acetylene (7.08 g, 72 mmol), triethylamine (200 mL) and DMF (80 mL). The mixture was stirred under nitrogen for 10 min, followed by addition of Pd(PPh3)2Cl2 (0.84 g, 1.2 mmol). The mixture was then stirred to 70 C. for 5 h, and then diluted with ethyl acetate (600 mL). The solution was washed with H2O (250 mL×2), brine (250 mL), dried over Na2SO4, and evaporated in vacuo to give crude product which was purified by flash chromatography (100% CH2Cl2 to 2% MeOH in CH2Cl2) to afford Compound 1c (2. 97 g, 78%) as a light brown solid. 1H NMR (CDCl3) delta 8.37 (s, 1H), 8.13 (d, J=5.7 Hz, 1H), 6.53 (d, J=5.6 Hz, 1H), 4.67 (bs, 2H), 0.27 (s, 9H). ES-MS m/z 191 (MH+). [0186] Into an ice-cold solution of 1c (1.35 g, 7.1 mmol) in THF (50 mL) was added 95% NaH (1.86 g, 8.5 mmol). The mixture was stirred at 0 C. for 10 min, rt for 10 min, then cooled back to 0 C. (Boc)2O (1.86 g, 8.5 mmol) was added and the mixture was stirred at 0 C. for 30 min and then rt for 2 h. Additional 95% NaH (0.08 g, 3.5 mmol) and (Boc)2O (0.2 g, 0.92 mmol) were added and the mixture was stirred at rt for another 2 h. The reaction was then quenched slowly with saturated NaHCO3 (10 mL), extracted with ethyl acetate (200 mL×2). The organic layer was washed with brine, dried over Na2SO4, and evaporated in vacuo. The crude product was purified by flash chromatography (EtOAc/hexane; 1:3) to give 1d (0.67 g). ES-MS m/z 219 (MH+). [0187] To a solution of 1d (1.3 g, 4.5 mmol) in DMF (20 mL) was added cupric iodide (0.85 g, 4.5 mmol). The mixture was stirred at 80 C. for 6 h and then filtered. The filtrate was extracted with ethyl acetate (100 mL×3), and the organic layer was washed with H2O, brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (Ethyl acetate/hexane; 1:3) to give Compound 1e (0.25 g, 26%). 1H NMR (CDCl3) delta 8.89 (s, 1H), 8.47 (d, J=5.8 Hz, 1H), 7.98 (d, J=5.7 Hz, 1H), 7.62 (d, J=3.7 Hz, 1H), 6.66 (d, J=3.7 Hz, 1H), 1.69 (s, 9H). ES-MS m/z 219 (MH+). [0188] To a solution of 1e (0.178 g, 0.82 mmol) in methylene chloride (5 mL) was added TFA (1.0 mL) slowly. The mixture was stirred at rt for 1.5 h, and The solvent was evaporated to obtain 5-azaindole 1f as a white solid (0.18 g, 95%). 1H NMR (CDCl3) delta 8.97 (s, 1H), 8.31 (d, J=5.7 Hz, 1H), 7.35 (d, J=5.7 Hz, 1H), 7.29 (m, 1H), 6.68 (d, J=3.3 Hz, 1H). ES-MS m/z 119 (MH+). [0189] A mixture of Compound 1f (0.26 g, 2.2 mmol) and cesium carbonate (1.43 g, 4.4 mmol) in DMF (10 mL) was stirred at rt for 10 min, and then 3-methoxypropylbromide (0.40 g, 2.64 mmol) was added. The reaction mixture was stirred at 60 C. for 3 h. The solvent was evaporated and the residue was partitioned between EtOAc (150 mL) and water (100 mL). The organic layer was washed with water (3×50 mL), brine (2×50 mL), then dried (Na2SO4) and evaporated in vacuo to give a brown oil. The crude product was purified by flash column chromatography (from 100% DCM to DCM/MeOH/NH4OH; 97:3:0.3) to afford Compound 1g (0.26 g, 62%) as light brown oil. 1H NMR (CDCl3) delta 8.91 (s, 1H), 8.31 (d, J=5.8 Hz, 1H), 7.27 (s, 1H), 7.11 (d, J=3.2 Hz, 1H), 6.60 (d, J=3.3 Hz, 1H), 4.25 (t, J=6.7 Hz, 2H), 3.32 (s, 3H), 3.25 (t, J=5.7 Hz, 2H), 2.05 (m, 2H). ES-MS m/z 191(MH+). [0190] Oxalyl chloride (3 mL) was added slowly to a solution of compound 1g (0.22 g, 1.14 mmol) in ether (5 mL). The mixture was heated to 48 C. in a pressure tube overnight. TLC shown that some starting materials were still present. Additional 0.5 mL of oxalyl chloride was added and stirring was continuted at 48 C. for another night. The mixture was then cooled down to rt, to which methanol (3 mL) was added. The mixture was heated to 48 C. and stirred for 2 h. The volatiles removed under vacuo and the residue was purified by flash chromatography (from 100% DCM to DCM/MeOH/NH4OH; 97:3:0.3) to afford Compound 1h (0.15 g, 48%) as a white solid. 1H NMR (CDCl3) delta 8.51 (d, J=5.8 Hz, 1H), 8.44 (s, 1H), 7.37 (m, 1H), 4.34 (t, J=6.8 Hz, 2H), 3.97 (s, 3H), 3.35 (s, 3H), 3.30 (t, J=5.7 Hz, 2H), 2.12 (m, 2H). ES-MS m/z 277 (MH+). [0191] The alpha-ketoester Compound 1h (53.8 mg, 0.20 mmol) and amide Compound 1i (23 mg, 0.14 mmol) were combined in dry THF (3 mL) under argon and cooled with an ice bath as a solution of 1.0 M potassium t-butoxide in THF (1 mL, 1 mmol) was added dropwise. The mixture was stirred at 0 C. for 30 …

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. 88511-27-7, 4-Amino-3-iodopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhang, Han-Cheng; Maryanoff, Bruce E.; Ye, Hong; US2004/192718; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 88511-27-7, 4-Amino-3-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, Recommanded Product: 88511-27-7, blongs to pyridine-derivatives compound. Recommanded Product: 88511-27-7

Step 2. To a 2 L 3-necked flask was added DMF (700 mL), triethylene diamine ( 168 g, 1 .5 mol), and 4-amino-3-iodopyridine (24, 1 10 g, 0.5 mol). The mixture was cooled with an ice-water bath and pyruvic acid (1 32 g, 1 .5 mol) was slowly added, followed by palladium acetate (4.49 g, 0.02 mol). Under nitrogen atmosphere, the mixture was heated to 1 15 C. The reaction generated effervescence. The reaction mixture was kept at 115- 120 C for 1 1 h, The mixture was concentrated under reduced pressure The residue was poured into water (500 mL), and concentrated HC1 was added to adjust pH to The above cake was added into 500 mL of water. Concentrated HCl was added (to ensure complete protonation) followed by 5 g of active carbon. The mixture was heated to reflux for 20 min and then filtration was performed while hot. The solid was discarded and the hot filtrate was placed in a refrigerator to allow the HCl salt of the desired product to precipitate. Upon cooling, filtration was performed which afforded a dark brown solid with a wet weight of 48 g as the HCl salt of the desired product. The solid was then added to 250 mL of water and the mixture was heated until a clear solution resulted. Solid NaOH was slowly added to adjust pH to 5-6, then active carbon and an addtional 500 mL of water was added. The mixture was heated to reflux for 30 min, then filtration was performed while hot. The resulting cake was added to 750 mL of water, heated to reflux, and filtered again. The cake thus obtained was discarded. The two batches of filtrate were combined and cooled in a refrigerator. The resulting precipitate was collected by vacuum filtration, then washed with ethanol to give the title compound as a slightly yellow solid (25 g, 31 %). MS (m/z, ES-): 161 . 1 [M-1], 323. 1 [2M-1]. 1H NMR (DMSO-d6, 400 MHz) delta 12.20 (br s, 1H), 8.97 (s, 1H), 8.27 (d, J = 5.6 Hz, 1 H), 7.41 (d, = 6.0 Hz, 1H), 7.23 (s, 1H).

The synthetic route of 88511-27-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; FORMA TM, LLC; BAIR, Kenneth W.; BAUMEISTER, Timm R.; BUCKMELTER, Alexandre J.; CLODFELTER, Karl H.; DRAGOVICH, Peter; GOSSELIN, Francis; GUNZNER-TOSTE, Janet; HAN, Bingsong; LIN, Jian; LIU, Xiongcai; REYNOLDS, Dominic J.; SMITH, Chase C.; WANG, Zhongguo; ZAK, Mark; ZHANG, Yamin; ZHAO, Guiling; ZHENG, Xiaozhang; YUEN, Po-Wai; WO2013/127266; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 88511-27-7, 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 88511-27-7, name is 4-Amino-3-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 3-iodopyridin-4-amine (6 g, 27.2 mmol) in dioxane (135 mL), (2,6-dichloropyridin-3-yl)boronic acid (7.29 g, 38.1 mmol), and 1M Na2CO3 aqueous solution (3 eq) were added andthe reaction mixture was degassed with argon for 20 mm. ThenBis(triphenylphosphine)palladium(ll) dichloride (3.79 g, 5.4 mmol) was added and the reactionmixture was heated at 100C for 16h. After completion of reaction, the reaction mixture wasfiltered through a celite pad and the filtrate was concentrated under reduced pressure to afford a residue that was dissolved in water and extracted with ethyl acetate. The organic layer was separated, dried over sodium sulphate and concentrated under reduced pressure to afford the crude product, which was further purified by silica gel (100:200 mesh) column chromatography toafford 2,6-dichloro-[3,3-bipyridin]-4-amine (ii) (2.9 g, Yield 44%).1H NMR (400 MHz, DMSO-d6) 66.04 (s, 2H), 6.62 (d, J= 5.8 Hz, 1H), 7.71 -7.55 (m, 1H), 7.94- 7.75 (m, 2H), 8.03 (d, J = 5.7 Hz, 1 H).MS (ESI) m/e (M+1): 240.05

According to the analysis of related databases, 88511-27-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB BIOPHARMA SPRL; MERCIER, Joel; VERMEIREN, Celine; (23 pag.)WO2018/24642; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 88511-27-7, 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.88511-27-7, name is 4-Amino-3-iodopyridine, molecular formula is C5H5IN2, molecular weight is 220.0111, as common compound, the synthetic route is as follows.

General procedure: In a typical experiment Pd(OAc)2 (5.6 mg, 0.025 mmol), triphenylphosphine (13.2 mg, 0.05 mmol), 4-amino-3-iodopyridine(1) (220 mg, 1.00 mmol), tert-butylamine (0.315 mL, 3.00 mmol)(or the given amount of primary or secondary amine (Table 1)) and triethylamine (0.5 mL) were dissolved in DMF (10 mL) under argon in a 100 mL autoclave. The atmosphere was changed to carbonmonoxide and pressurized to 40 bar. The reaction was conducted for the given reaction time upon stirring at 50C and analysed by TLC. The autoclave was vented, the reaction mixture was concen-trated and evaporated to dryness. The residue was dissolved in chloroform (20 mL) and washed with water (320 mL). The organic phase was dried over Na2SO4, filtered and evaporated to a solid material. All compounds were subjected to column chromatography ((Silicagel 60 (Merck), 0.063 e 0.200 mm); MeOH/CHCl3 orMeOH/EtOAc/CHCl3 (the exact ratios are specied in Characterization (4.4.) for each compound)).

Statistics shows that 88511-27-7 is playing an increasingly important role. we look forward to future research findings about 4-Amino-3-iodopyridine.

Reference:
Article; Szoke, Gyoengyi; Takacs, Attila; Berente, Zoltan; Petz, Andrea; Kollar, Laszlo; Tetrahedron; vol. 72; 22; (2016); p. 3063 – 3067;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 88511-27-7, 4-Amino-3-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, Safety of 4-Amino-3-iodopyridine, blongs to pyridine-derivatives compound. Safety of 4-Amino-3-iodopyridine

Example 3; 8-Eth l-6,7,8,9-tetrahydro-5H-pyrido[4,3-b]indoleSi(OEt) (284 mg, 1 .36 mmol) was added to a solution of 4-amino-3-iodopyridine (300 mg, 1 .36 mmol), 4-ethylcyclohexanone (344 mg, 2.72 mmol) and PPTS (68 mg, 0.27 mmol) in pyridine (3 ml). The mixture was flushed with N2 and heated at 160C under microwave for 45 min. Pd(PPh3) (78 mg, 0.068 mmol) and dicyclohexylmethylamine (319 mg, 1 .63 mmol) were added to the reaction mixture. The mixture was flushed with N2, then heated at 170C under microwave for 2 hours. The reaction mixture was cooled and partitioned between H2O and EtOAc. The organic phase was washed with brine, dried over Na2SO4 and concentrated. The residue was subjected to chromatography (silica gel treated with Et3N in DCM, eluting with MeOH in DCM) to afford 220 mg of impure product, which was purified again with HPLC (Ci8, eluting with 10-100% CH3CN in H2O with 0.1 % TFA). 142 mg of gel was obtained from pure fractions. The gel was treated with MeOH and concentrated to give the title compound as a white crystalline solid (142 mg, TFA salt, 33%, hygroscopic).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,88511-27-7, 4-Amino-3-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; SANOFI; GROSS, Alexandre; LI, Ronghua; MAJID, Tahir Nadeem; MOORCROFT, Neil David; YU, Kin T.; ZILBERSTEIN, Asher; WO2011/84439; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem