Tag: M.W=200-300

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 1150617-63-2 as follows. COA of Formula: C7H7ClIN

To a solution of 5-chloro-2-iodo-3-methylaniline (325 mg, 1.21 mmol), PEPPSI-IPr (50.5 mg, 0.0729 mmol) and sodium tert-butoxide (193 mg, 1.94 mmol) in toluene (4 mL) is added 2-bromopropene (0.136 mL, 1.52 mmol). The mixture is heated at 175C for 15 min in the microwave, then at 215C for 20 min. The RM is concentrated under reduced pressure, and purified by FC, eluting with heptane/DCM 1 :0 to 3:1. This afforded the title compound as a yellow solid (71 mg, 33%). LC-MS A: tR = 0.89 min; [M+H]+ = 180.29. A.1.60. 6-Chloro-N-(2-(5,7-difluoro-2,4-dimethyl-1H-indol-1-yl)ethyl)pyrimidin-4-amine The title compound is prepared according to the synthesis of A.1.1. described above using 2-(5,7-difluoro-2,4- dimethyl-1 H-indol-1-yl)ethan-1-amine; LC-MS A: tR = 0.94 min; [M+H]+ = 336.96.

According to the analysis of related databases, 1150617-63-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; FRETZ, Heinz; LYOTHIER, Isabelle; POTHIER, Julien; RICHARD-BILDSTEIN, Sylvia; SIFFERLEN, Thierry; WYDER PETERS, Lorenza; POZZI, Davide; CORMINBOEUF, Olivier; (306 pag.)WO2017/85198; (2017); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 172681-47-9, name is 2-Amino-6-iodotoluene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 2-Amino-6-iodotoluene

B2pin2 (140 mg, 0.55mmol, 1.1 equiv) and aniline 17 (117 mg, 0.5 mmol, 1.0 equiv) were weighed in a 25mL round-bottom flask. MeCN (2mL) and t-BuONO (86 mg, 0.75 mmol, 1.5 equiv) were then added insuccession. The resulting reaction solution was stirred for 3 h at 80 C (N2 evolution completed within 5 to15 min). The solution was then concentrated under reduced pressure, and the crude residue was purifiedby flash chromatography (silica gel, hexane/EtOAc = 40:1) to give pinacol boronate ester 18 (91.2 mg) in53% yield. The following deprotection and dean-stark procedure was same as preparing 1t.23

The synthetic route of 172681-47-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Renhe; Liu, Feipeng; Dong, Guangbin; Chem; vol. 5; 4; (2019); p. 929 – 939;,
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Synthetic Route of 52914-23-5,Some common heterocyclic compound, 52914-23-5, name is 2-(4-Iodophenyl)ethanol, molecular formula is C8H9IO, 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 1.24 g (5 mmol) of 2-(4-iodophenyl)ethanol, 0.62 g (5.25 mmol) of 7-azaindole, 2.33 g (11.0 mmol) of potassium phosphate, 0.082 g (1.0 mmol) of N,N’-dimethylethylenediamine and 0.095 g (0.50 mmol) of cuprous iodide in 4 ml of toluene is heated at 80 C. overnight with thorough stirring under an argon atmosphere. The mixture is cooled to ambient temperature and diluted with 150 ml of ethyl acetate and 50 ml of water. After the phases have settled and been separated, the organic phase is washed with 25 ml of water and 25 ml of saturated aqueous sodium chloride solution. It is dried over sodium sulphate and evaporated to dryness. The residue is purified by chromatography on silica gel, eluting with a 70/30 then 60/40 and 50/50 mixture of cyclohexane and ethyl acetate, to give 1.05 g of product in the form of an oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Iodophenyl)ethanol, its application will become more common.

Reference:
Patent; Sanofi-Aventis; US2006/14830; (2006); A1;,
Iodide – Wikipedia,
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Electric Literature of 1097871-23-2, These common heterocyclic compound, 1097871-23-2, name is 1-Chloro-2,5-difluoro-4-iodobenzene, 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.

49-(4-methoxy)-10 borate 1 mmol,1-mmol-4-iododifluorobenzene 1 mmol, tetrakis(triphenylphosphine)palladium 0.1 mmol, toluene 40 mL,10 mL of ethanol and 340 mmol of K2CO (formed as a solution with 10 mL of distilled water) were added to the reaction flask, and then the system was evacuated and protected with nitrogen.The reaction was carried out at 100 C for 12 hours.After the end of the reaction, extraction, rotary distillation, column chromatography (eluent: n-hexane / dichloromethane = 1:1),Recrystallization gave the product A7.The yield was 69%.5A70.5mmol, boranoic acid pinacol ester 1.5mmol,Palladium acetate 0.05 mmol, 2-dicyclohexylphosphine-2′, 6′-dimethoxybiphenyl 0.1 mmol,1.5 mmol of potassium acetate and 25 mL of 1,4-dioxane were added to the reaction flask.The system is then evacuated, protected by nitrogen, and reacted at 90 C for 12 hours.After the reaction is over, extract, spin,Column chromatography (eluent: n-hexane / dichloromethane = 2:1),Recrystallization gave the product B7.The yield was 65%.6 The final product g is obtained by Suzuki coupling reaction:B70.25mmol, the product obtained in step 2, namely 9-bromo-10-(4-cyano)benzoquinone 0.21mmol,Catalyst tetrakis(triphenyl)phosphine palladium 0.03 mmol,Toluene 15mL, ethanol 5mL, K2CO38.4mmol (formed into solution with 5mL distilled water),It was added to the reaction flask and refluxed at 100 C for 12 h under the protection of nitrogen.After the reaction is completed, methanol is washed with hot water, suction filtered, and toluene is recrystallized.Sublimation gives the final product.The yield was 58%.The molecular formula is C48H29F2NO

The synthetic route of 1097871-23-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shaanxi Normal University; Hu Jianyong; Zhang Jiali; Zhao Zhen; (25 pag.)CN109678759; (2019); A;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 69518-17-8, name is 4-Iodophthalonitrile belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 4-Iodophthalonitrile

EXAMPLE 71 (1S,2R)-4′-(2-Hydroxy-1-methyl-4-pyridin-3-ylbutoxy)biphenyl-3,4-dicarbonitrile Prepared according to the method described in Example 12b) from (1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid (0.197 g, Example 33), 4-iodo-1,2-dicyanobenzene (0.421 g, Can. J. Chem., 1985, 63, 3057), 2M aqueous sodium carbonate (0.50 ml) and tetrakis(triphenylphosphine)palladium (0) (0.054 g) in ethanol (3 ml). The reaction mixture was heated in a sealed vial at 90 C. for 4 hours. After cooling, the solution was concentrated under reduced pressure and the residue purified by chromatography over silica eluding with ethyl acetate. The residue was further purified by chromatography over silica gel eluding with dichloromethane:2-propanol (19:1). The residue was then further purified by reverse-phase HPLC eluding a gradient of 25-100% acetonitrile in 0.1 w/v aqueous ammonium acetate solution. The HPLC fractions were concentrated under reduced pressure, the residue dissolved in dichloromethane, filtered and concentrated under reduced pressure. The residue was triturated with ether to give the title to compound as a solid (0.060 g). m.p. 135.5-137 C. MS (APCI) 384 (M+H)+ 1H NMR (DMSO) 8.47-8.43(2H, m); 8.38(1H, dd); 8.25-8.12(2H, m); 7.79(2H, d), 7.63(1H, dt); 7.30(1H, dd); 7.06(2H, d); 5.03(1H, d); 4.41(1H, quintet); 3.63-3.5(1H, m); 2.9-2.75(1H, m); 2.75-2.6(1H, m); 1.95-1.8(1H, m); 1.75-1.55(1H, m); 1.24(3H, d).

The synthetic route of 69518-17-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AstraZeneca AB; US6300352; (2001); B1;,
Iodide – Wikipedia,
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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 351447-07-9 as follows. SDS of cas: 351447-07-9

(Example 1 Synthesis of Compounds 1-42, 1-96, and I-51) [Show Image]Step 1 To a solution of Compound (5) (1.90 g, 7.25 mmol) in tetrahydrofuran (20mL), phenylisocyanate (1.0mL, 9.43mmol) and triethylamine (1.5 mL, 10.9 mmol) were added. The solution was then stirred at room temperature for 1 hour. The precipitated powder was filtered, and then washed with water. The resulting powder was further washed with diethyl ether to yield Compound 1-42 (1.95 g, 63%) as a white powder. 1H-NMR (DMSO-d6) delta12.13 (1H, s), 7.57 (2H, d, J = 8.4 Hz), 7.45 (1H, d, J = 8.1 Hz), 7.37 (2H, t, J = 7.5 Hz), 7.17 (1H, d, J = 8.4 Hz), 7.08 (1H, t, J = 7.2 Hz), 4.28 (2H, br s), 4.03 (2H, br s) LC/MS (Method A): 2.54 min, [M+H]+ = 382.3.

According to the analysis of related databases, 351447-07-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shionogi & Co., Ltd.; EP2341052; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 1097871-23-2, 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. 1097871-23-2, name is 1-Chloro-2,5-difluoro-4-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of (S)-N-((S)-(4-Chloro-2,5-difluorophenyl)(3-fluorooxetan-3-yl)methyl)-2-methylpropane-2-sulfinamide To an oven dried, 100 mL, round bottom flask, under a nitrogen atmosphere, was added 1-chloro-2,5-difluoro-4-iodobenzene (2.41 g, 8.77 mmol) in anhydrous THF (35 mL). The resulting solution was cooled to -100 C. with an ether/liquid nitrogen bath, and then n-butyllithium (1.6M in hexanes, 5.48 mL, 8.77 mmol) was added dropwise, keeping the internal temperature between -90 and -100 C. The resulting yellow mixture was stirred between -90 and -100 C. for 30 minutes, and then (S,E)-N-((3-fluorooxetan-3-yl)methylene)-2-methylpropane-2-sulfinamide (2.0 g, 9.65 mmol) in THF (5 mL) was added dropwise via syringe, keeping the internal temperature between -90 and -100 C. The resulting mixture was stirred between -90 and -100 C. for 30 minutes and then quenched at the same temperature by dropwise addition of saturated ammonium chloride (25 mL). The mixture was diluted with water (50 mL) and ethyl acetate (50 mL). The layers were shaken and separated and the organic phase was washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated to a viscous nearly colorless oil which was purified with silica gel using a gradient to 50% ethyl acetate/hexanes providing (S)-N-((S)-(4-chloro-2,5-difluorophenyl)(3-fluorooxetan-3-yl)methyl)-2-methylpropane-2-sulfinamide (1.64 g, 4.6 mmol) the desired single diastereomer, as a white foam. 1H NMR (400 MHz, Methanol-d4) delta 7.58-7.37 (m, 2H), 5.28 (d, J=26.1 Hz, 1H), 4.99-4.89 (m, 1H), 4.85-4.76 (m, 1H), 4.69-4.50 (m, 2H), 1.21 (s, 9H). LCMS-ESI (POS.) m/z: 356.10 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis 1-Chloro-2,5-difluoro-4-iodobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AMGEN INC.; CYTOKINETICS, INC.; Ashcraft, Luke; Boezio, Alessandro; Butler, John; Chandra, Aroop; Chuang, Chihyuan; Collibee, Scott E.; Debenedetto, Mikkel; DiMassa, Vincent; Graceffa, Russell; Malinowski, Justin; Moebius, David; Morgan, Bradley P.; Payette, Joshua; Romero, Antonio; St. Jean, JR., David; Vargas, Richard; Yeoman, John; Zhang, Hanmo; (146 pag.)US2019/77793; (2019); A1;,
Iodide – Wikipedia,
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Application of 52107-68-3, These common heterocyclic compound, 52107-68-3, name is 5-Iodo-2-methylbenzonitrile, 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 stirred slurry of sodium hydride (60% dispersion in mineral oil, 480 mg, 12.0 mmol) in DME (3.0 mL)was refluxed. 5-iodo-2-methylbenzonitrile (729 mg, 3.00 mmol), methyl benzoate (544 mg, 4.00 mmol),and DME (3.0 mL) were added to the slurry. After a catalytic amount of MeOH was added, the mixture was refluxed for 7 h. The mixture was cooled to 0C. water (10 mL) was added to quench the reactionand then 2 M HCl (10 mL) was added. The resulting mixture was diluted with EtOAc (30 mL). The aqueous layer was extracted with EtOAc (2×30 mL). The combined organic layers were washed with brine (10 mL), dried over Na2SO4, and filtered. The solvents were evaporated in vacuo. The crude product was purified by recrystallization from ethanol to give 5-iodo-2-(2-oxo-2-phenylethyl)benzonitrile (5g)(635 mg, 61%). Yellow white solid. Mp 134-136C. 1H NMR (400 MHz, CDCl3): delta = 7.98-8.04 (m, 3H),7.87-7.89 (m, 1H), 7.60-7.64 (m, 1H), 7.49-7.53 (m, 2H), 7.10-7.13 (m, 1H), 4.49 (s, 2H). 13C NMR (100MHz, CDCl3): delta = 194.7, 141.8, 140.8, 138.1, 136.0, 133.8, 132.6, 128.8, 128.3, 116.3, 115.6, 91.7, 43.2.IR (KBr): 3097, 3056, 3033, 2951, 2884, 2230, 1688, 1594, 1479, 1448, 1416, 1385, 1332, 1204, 1110,988, 906, 868, 837, 806, 752 cm-1. HRMS (EI): Calcd for C15H10INO 346.9807 (M)+, found 346.9820.

Statistics shows that 5-Iodo-2-methylbenzonitrile is playing an increasingly important role. we look forward to future research findings about 52107-68-3.

Reference:
Article; Yashiro, Kai; Sakata, Keito; Hachiya, Iwao; Shimizu, Makoto; Heterocycles; vol. 92; 11; (2016); p. 2032 – 2046;,
Iodide – Wikipedia,
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Synthetic Route of 773136-66-6, 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 773136-66-6 as follows.

Add NaH (3.71 g, 92.8 mmol, 60.0% purity, 1.3e q) to dry THF (131.0 mL).Compound 2 (21.0 g, 71.4 mmol, 1 eq) and 1-vinylpyrrolidin-2-one (8.49 g, 76.4 mm ol, 8.17 mL, 1.07 eq).The mixture was stirred at 80 C for 3 hours.It was then cooled to room temperature.Then 10% HCl solution (30 mL) was slowly added and stirred at 100 C for 10 hours.The progress of the reaction was detected by TLC (P etroleum ether/Ethyl acetate = 4/1, Rf = 0.68).When the reaction is over,In the condition of an ice bath,Gradually add 1M NaOH solution,The pH of the reaction solution was adjusted to 8.0.Further extraction with DCM (50.0 mL x 2),And by column chromatography (SiO2,Petroleum ether/Ethyl acetate=8/1to 5/1),Obtained white compound 3 (1.60 g, 5.53 mmol,7.75% yield).Figure 4 shows the results of TLC chromatography for this reaction.The NMR data for Compound 3 is:

According to the analysis of related databases, 773136-66-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Health Medical School; Tang Dewei; Huang Gang; Huang Chen; Wu Xingyu; Yu Meicen; Li Yanjiao; (18 pag.)CN109942582; (2019); A;,
Iodide – Wikipedia,
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Electric Literature of 133232-56-1,Some common heterocyclic compound, 133232-56-1, name is 3-Iodo-2-methylbenzoic acid, molecular formula is C8H7IO2, 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 19{fl-Cyano-4-hydroxy-8-(4-methoxy-phenoxy)-isoquinoline-3-carbonyll-amino}-acetic acid a. 3-Iodo-2-methyl-benzoic acid methyl ester[0235] A mixture of 3-iodo-2-methyl-benzoic acid (90 mmol, 23.6 g), methanol (250 mL), and concentrated sulfuric acid (13 mL) was re fluxed with stirring for 40 h before it was concentrated in vacuo. The residue was dissolved in ethyl acetate and the mixture was neutralized by adding small portions of a saturated aqueous NaHCOs solution with stirring. The organic phase was dried over MgSO4 and concentrated in vacuo to give the title compound as a yellowish oil (24.3 g); 1H NMR (CDCl3, 200 MHz): delta = 7.96 (d, 1 H), 7.71 (d, 1 H), 6.91 (t, 1 H), 3.89 (s, 3 H), 2.66 (s, 3 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Iodo-2-methylbenzoic acid, its application will become more common.

Reference:
Patent; FIBROGEN, INC.; WO2007/90068; (2007); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com