Tag: M.W=200-300

Application of 2142-70-3, These common heterocyclic compound, 2142-70-3, name is 1-(2-Iodophenyl)ethanone, 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.

[283] To a solution of 1-(2-iodophenyl)ethanone (4.0 g, 16.3 mmol) in a mixed solvent of chloroform (50 mL) and ethyl acetate (50 mL) was added cupric bromide (7.26 g, 32.5 mmol). The resulted mixture was stirred at reflux for 3h, then cooled down to roomtemperature, filtered, the filter cake was washed with ethyl acetate (50 mL), the filtrate was concentrated, the residue was purified by flash chromatography (petroleum ether: ethyl acetate= 50:1) to afford 2-bromo-1-(2-iodophenyl) ethanone (4.65 g, yield: 88%) as a light yellow oil.[284] ?H NIVIR (400 IVIFIz, CDC13-d): 7.98 (d, J = 8.0 Hz, 1H), 7.47 (d, J = 8.0 Hz, 2H), 7.19-7.21 (m, 1 H), 4.47 (s, 2H).

The synthetic route of 2142-70-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHANGHAI DE NOVO PHARMATECH CO.,LTD.; LI, Qun; GAO, Daxin; (158 pag.)WO2016/131380; (2016); A1;,
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Related Products of 2265-91-0,Some common heterocyclic compound, 2265-91-0, name is 1,3-Difluoro-5-iodobenzene, molecular formula is C6H3F2I, 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.

10297] To a stirred solution of 5-(but-i-yn-i-yl)-i-(tetra- hydro-2H-pyran-2-yl)-1H-indazole (0.4 g, 1.574 mmol, Example 1, Step-3) in 2-methyl THF (5 mE), was added bis(pinacolato)diboron (0.44 g, 1.732 mmol), tetrakis(triphenylphosphine)platinum(0) (14.6 mg, 0.0118 mmol) under nitrogen atmosphere, reaction mixture was heated at 90 C. for 5 h. Afier completion of reaction (monitored by TEC), reaction mixture was allowed to cool to 4 C. and tert-butyl (2-(4-iodophenoxy)ethyl)carbamate (571 mg, 1.574 mmol, Example 3, Step-2), bis(triphenylphosphine)palladium(II) dichloride (55 mg, 0.078 mmol), cesium carbonate (1.023 g, 3.140 mmol) and 2-methyl THF (5 mE) were added. This mixture was degassed with nitrogen and water (1.2 mE) was added. Reaction mixture was stirred at room temperature for 16 h. Afier completion of reaction (monitored by TEC), i,3-difluoro-5-iodobenzene (528 mg, 2.20 mmol) and 4M aqueous KOH (3 mE) were added and the mixture was degassed with nitrogen and heated at 70 C. for 5 h. Upon completion, the reaction mixture was filtered through a celite/silicagel pad and washed with EtOAc. The filtrate was washed with water, brine, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (2:8 EtOAc in n-hexane) to give title compound of Ex. 5 Step-i (500 mg, 54%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3-Difluoro-5-iodobenzene, its application will become more common.

Reference:
Patent; Eisai R&D Management Co., Ltd.; BOCK, Mark; HAO, Ming-Hong; KORPAL, Manav; NYAVANANDI, Vijay Kumar; PUYANG, Xiaoling; SAMAJDAR, Susanta; SMITH, Peter Gerard; WANG, John; ZHENG, Guo Zhu; ZHU, Ping; (141 pag.)US2016/347717; (2016); A1;,
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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. 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H3ClFI

Preparation 9 IB: (2-Chloro-4-fluorophenyl)(3-fluoro-4-(pyrimidin-5-yl)pyridin-2- yl)methanoneTo a solution of 2-chloro-4-fluoro-l-iodobenzene (0.307 g, 1.199 mmol) in THF (Volume: 1.622 ml) cooled to -10 C was added isopropylmagnesium chloride, 2M in THF (0.699 ml, 1.399 mmol) in one portion. After 30 min, 3-fluoro-4-(pyrimidin-5- yl)picolinonitrile (0.200 g, 0.999 mmol) was added. The reaction mixture was stirred at -10 C for 30 min, then allowed to warm to room temperature and stirred overnight. Water and ice were carefully added, followed by acidification with 6 M HC1. After stirring for 1 hr, CH2C12 was added and the pH was adjusted to 8.5 with aqueous 4 M NaOH. The layers were separated. The aqueous phase was extracted with CH2CI2 (5X). Organics combined, dried over Na2S04, filtered, and concentrated to afford an orange residue. The crude material was dissolved in a minimal amount of CH2CI2 to be chromatographed. Purification of the crude material by silica gel chromatography using an ISCO machine (24 g column, 35 mL/min, 60-100% EtOAc in hexanes over 23 min, tr = 9 min) gave the title compound (0.029 g, 0.074 mmol, 7.44% yield) as an orange solid.

According to the analysis of related databases, 101335-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; HUANG, Audris; VELAPARTHI, Upender; LIU, Peiying; WO2013/49263; (2013); A1;,
Iodide – Wikipedia,
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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. 25245-35-6, name is 2-Iodo-1,4-dimethoxybenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H9IO2

(3) Compound C (20.21 g, 98.0 mmol) was dissolved in benzene (150 mL), and 2,5-dimethoxyiodobenzene (27.16 g, 102.9 mmol), Pd (PPh3) was sequentially added at -15 C. 2Cl2 (0.69 g, 0.98 mmol), CuI (0.93 g, 4.9 mmol) and DIPEA (40 mL, 391 mmol),Then it was raised to 20 C to 30 C and stirred for 4 h.The reaction was quenched with EtOAc EtOAc (EtOAc)The combined organic layers were washed with brine (30 mL)After concentration under reduced pressure, the mixture was separated by column chromatography (hexane: ethyl acetate = 16:1).25.16 g of compound D was obtained in a yield of 75%(Rf = 0.38, n-hexane: ethyl acetate = 8:1).Among them, the detection data of compound D is as follows:

The synthetic route of 25245-35-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing University Shenzhen Sheng Yuan; Shao Wenbin; Huang Jun; Guo Kai; Zhang Weibin; Gong Jianxian; Yang Zhen; (47 pag.)CN108484638; (2018); A;,
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Related Products of 111771-08-5, A common heterocyclic compound, 111771-08-5, name is 2-Fluoro-6-iodobenzoic acid, molecular formula is C7H4FIO2, 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.

W-Ethyl-2-fluoro-6-iodo-W-[(S)-1 -methyl-2-(5-trifluoromethyl-pyridin-2-yloxy)-ethyn (0350) (0351) D-1.1 (150 mg, 0.56 mmol) is dissolved in dry DCM (3.0 mL). Under stirring oxalylchloride (846 mg, 1 .13 mmol) and a drop of DMF are added and the mixture is stirred for 2 h. The mixture is concentrated and the residue is taken up with dry DCM (3.0 mL). The resulting mixture is added dropwise to a mixture of B-1 (145 mg, 0.51 mmol) and DIPEA (390 mu, 2.30 mmol) in DCM (4.0 mL) at 0C. The cold bath is removed and the mixture is stirred for 2 h. The crude product is diluted with DCM and washed with NH4CI (sat. solution), KHC03 (sat. solution) and water. The organic phase is dried and concentrated. The residue is purified by flash column chromatography (using a solvent gradient from 100% Cyclohexane to Cyclohexane/EA 65/35) to afford 160 mg of compound D-1. ESI-MS: 497 [M+H]+; HPLC (Rt): 1.21 min (Method P).

The synthetic route of 111771-08-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; RIETHER, Doris; FERRARA, Marco; HEINE, Niklas; LESSEL, Uta; NICHOLSON, Janet Rachel; PEKCEC, Anton; SCHEUERER, Stefan; (69 pag.)WO2017/178341; (2017); A1;,
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Synthetic Route of 696-41-3, These common heterocyclic compound, 696-41-3, name is 3-Iodobenzaldehyde, 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.

General procedure: To a 10 mL glass tube aryl halide (1 mmol), K4FeCN6(0.6 mmol,220 mg), K2CO3(1.5 mmol, 207 mg), catalyst (10 mg), and 2 mL DMFwere added and mixture was stirred for appropriate reaction timeat 120C under argon atmosphere. The progress of the reactionwas monitored by GC analysis. After completion of the reaction,reaction mixture was washed with 5 mL water and crude productwas isolated using dichloromethane (5¡Á 1 mL). Organic extractswere combined together, evaporated and purified by flash chro-matography using hexane/EtOAc to give the desired aryl cyanideproducts.

The synthetic route of 696-41-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gholinejad, Mohammad; Aminianfar, Afsaneh; Journal of Molecular Catalysis A: Chemical; vol. 397; (2015); p. 106 – 113;,
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Electric Literature of 3032-81-3, 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. 3032-81-3, name is 1,3-Dichloro-5-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of N-picolinoylcyclododecylamine (3) (0.2 mmol, 57.6 mg), aryl iodide4 (0.4 mmol), Ag2CO3 (0.3 mmol, 82.7 mg), and Pd(OAc)2 (0.04 mmol, 9.0 mg)in t-AmOH (1 mL) was stirred for 48 h at 110 C in the dark. After dilution withEtOAc, the mixture was filtered and the filtrate was concentrated in vacuo. Theresidue was purified by preparative TLC (EtOAc/CHCl3/hexane = 1:1:8) to givethe corresponding product. Trans-3-(4-nitrophenyl)-N-picolinoylcyclododecylamine[5a(trans)]

The synthetic route of 1,3-Dichloro-5-iodobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Seki, Atsushi; Tetrahedron Letters; vol. 58; 45; (2017); p. 4232 – 4235;,
Iodide – Wikipedia,
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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. 14452-30-3, name is 1-(3-Iodophenyl)ethanone, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 14452-30-3

To a stirred solution of l-(3-iodophenyl) ethanone 22-1 (200 mg, 0.81 mmol) in DMF (3 mL) was added allyl alcohol (252 mg, 4.06 mmol), AgOAc (137 mg,0.81 mmol), TPP (21 mg, 0.081 mmol). The mixture was purged with argon for 15 min and Pd(OAc)2 (27 mg, 0.04 mmol) was added at RT. The reaction mixture was warmed to 70 C for 16 hr under nitrogen atmosphere. The reaction mixture was diluted with water (10 mL) extracted with EtOAc (3 X 50 mL), the combined organic layers were washed with brine (2 X 40 mL) and dried over Na2S04 and concentrated. The residue was purified by column chromatography (100-200 silica) using 20-25% EtOAc/Pet. ether to afford 22-2 (100 mg, 0.56, 69.9% yield) as a colorless liquid. MS=177.1 [M+l]+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 14452-30-3.

Reference:
Patent; COCRYSTAL PHARMA, INC.; JACOBSON, Irina C.; FEESE, Michael D.; LEE, Sam S.; (169 pag.)WO2016/154241; (2016); A1;,
Iodide – Wikipedia,
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Synthetic Route of 5471-81-8,Some common heterocyclic compound, 5471-81-8, name is Methyl 4-iodo-3-methylbenzoate, molecular formula is C9H9IO2, 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.

Under a protective atmosphere of inert gas, Pd(OAc)2 (2.2 mg, 10 mol%), XPhos (19.1 mg, 20 mol%), NBE-CO2K (3.5 mg, were added to a 4.0 mL reaction flask equipped with a magnetic stir bar. 10mol%),Methyl 3-methyl-4-iodobenzoate (0.2 mmol, 1.0 equiv.),1,2-epoxyhexane (0.6 mmol, 3.0 equiv.) and dry N-methylpyrrolidone (1.0 mL). The reaction flask was capped and stirred at room temperature for about 5 minutes, after which the mixture was heated to 80 C and stirred for 24 hours. Time. After the reaction vessel was cooled to room temperature, it was diluted with water (10 mL). Filter and concentrate under vacuum. Purified by column chromatography, the eluent was petroleum ether: ethyl acetate = 20:1 (v/v).35 mg of methyl 7-methyl-2-n-butyl-2,3-dihydrobenzofuran-5-carboxylate (light yellow oily liquid, yield 71%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-iodo-3-methylbenzoate, its application will become more common.

Reference:
Patent; Wuhan University; Zhou Qianghui; Wu Chenggui; Cheng Honggang; (20 pag.)CN108329285; (2018); A;,
Iodide – Wikipedia,
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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. 52548-63-7, name is 5-Fluoro-2-iodobenzoic acid, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H4FIO2

To a solution of 1H-pyrrolo[2,3-c]pyridine (70 g, 0.59 mol) in MeOH (1,050 mL) and H2O (350 mL) was added KOH (83 g, 1.48 mol) and tert-butyl 3-oxopiperidine-1- carboxylate (259 g, 1.30 mol). The resulting mixture was stirred at 75-80 oC (oil bath temperature) for 18 h. The reaction mixture was concentrated under reduced pressure to remove MeOH, then H2O (700 mL) was added and the mixture was extracted with EtOAc (3 ¡Á 1000 mL). The organic layers were filtered and the filtered cake was washed with EtOAc (2 ¡Á 150 mL) to afford tert-butyl 5-(1H-pyrrolo[2,3-c]pyridin-3-yl)-3,4- dihydropyridine-1(2H)-carboxylate (75 g, 42% yield) as white solid. The organic layer was concentrated under reduced pressure to about 250 mL. The residue was stirred at 5-9 oC for 18 h. The residue was filtered and the filtered cake was washed with EtOAc (2 ¡Á 60 mL) to give a mixture of tert-butyl 5-(1H-pyrrolo[2,3-c]pyridin-3-yl)-3,6- dihydropyridine-1(2H)-carboxylate and tert-butyl 5-(1H-pyrrolo[2,3-c]pyridin-3-yl)-3,4- dihydropyridine-1(2H)-carboxylate (1:3.5 via LCMS; (28 g, 16% yield) as white solid. tert-butyl 5-(1H-pyrrolo[2,3-c]pyridin-3-yl)-3,4-dihydropyridine-1(2H)- carboxylate: Yield: 75 g (42%); Rt value: 0.570 (LCMS Method C); (M+H)+ = 300.1; 1H NMR (MeOD, 400 MHz): delta ppm 8.65-8.70 (d, J = 2.8 Hz, 1H), 8.05-8.15 (d, J = 5.6 Hz, 1H), 7.70-7.90 (m, 1H), 7.54 (s, 1H), 7.35-7.50 (m, 1H), 3.60-3.75 (m, 2H), 2.50-2.60 (t, J = 5.6 Hz, 2H), 2.00-2.10 (m,2H), 1.55-1.60 (m, 9H). Mixture of tert-butyl 5-(1H-pyrrolo[2,3-c]pyridin-3-yl)-3,6-dihydropyridine- 1(2H)-carboxylate and tert-butyl 5-(1H-pyrrolo[2,3-c]pyridin-3-yl)-3,4-dihydropyridine- 1(2H)-carboxylate: Rt value: 0.568 (LCMS Method C); (M+H)+ = 300.1. A suspension of tert-butyl 5-(1H-pyrrolo[2,3-c]pyridin-3-yl)-3,4-dihydropyridine- 1(2H)-carboxylate and tert-butyl 5-(1H-pyrrolo[2,3-c]pyridin-3-yl)-3,6-dihydropyridine- 1(2H)-carboxylate (1 g, 3.34 mmol, ~10:1 ratio of isomers), 5-fluoro-2-iodobenzoic acid (977 mg, 3.67 mmol), K2CO3 (1.15 g, 8.33 mmol), CuI (63 mg, 0.334 mmol) and 1,10- phenanthroline (60 mg, 0.334 mmol) in DMF (13 mL, 0.26 M reaction concentration) was degassed with N2 for 15 min. The reaction mixture was then placed under N2 and heated to 70 oC for 24 h. The reaction was then cooled to room temperature and filtered through a plug of Celite using a small amount of DMF to rinse the filter cake. The DMF solution was cooled to 0 oC and a 1N aq. HCl solution (~10 mL) was added, maintaining a pH of ~5, followed by the addition of H2O (~10 mL) and EtOAc for the extraction. The EtOAc layer was separated and the aqueous layer (pH~5) was extracted three additional times with EtOAc. The EtOAc layers were combined and washed with H2O followed by brine. After drying over Na2SO4, the EtOAc layer was evaporated and the resulting residue was dried under high vacuum overnight to afford ~2 grams of crude 2-(3-(1-(tert-butoxycarbonyl)-1,4,5,6-tetrahydropyridin-3-yl)-1H-pyrrolo[2,3-c]pyridin- 1-yl)-5-fluorobenzoic acid and 2-(3-(1-(tert-butoxycarbonyl)-1,2,5,6-tetrahydropyridin-3- yl)-1H-pyrrolo[2,3-c]pyridin-1-yl)-5-fluorobenzoic acid (>10:1 ratio of isomers). The crude material was used directly for the next step without further purification. LCMS: 5.748 min (LCMS Method G): 438.47 (M + 1).1H NMR (400 MHz, CDCl3): delta 8.52-8.48 (m, 1H), 8.20-8.15 (m, 1H), 8.07 (bs, 1H), 8.01 (s, 1H), 7.85 (d, 1H, J = 8.4 Hz), 7.76 (s, 1H), 7.55 (bs, 1H), 7.42 (d, 1H, J = 5.2 Hz), 3.67 (bs, 2H), 2.50-2.47 (m, 2H), 2.06-2.01 (m, 2H), 1.54 (s, 9H).

According to the analysis of related databases, 52548-63-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CACATIAN, Salvacion; CLAREMON, David A.; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen D.; SINGH, Suresh B.; VENKATRAMAN, Shankar; YUAN, Jing; ZHENG, Yajun; ZHUANG, Linghang; (285 pag.)WO2018/53267; (2018); A1;,
Iodide – Wikipedia,
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