Month: March 2021

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. 31599-61-8, name is 4-Iodo-1,2-dimethylbenzene, A new synthetic method of this compound is introduced below., Formula: C8H9I

General procedure: Aryl-halide (0.2 mmol, 1 equiv.), Ir(dtbbpy)(ppy)2PF6 (1.8 mg, 0.002 mmol, 1 mol %), NiI2 (3.1 mg, 0.01mmol, 5 mol %), DMSO (2.0 mL) was added to a 10 mL schlenk flask equipped with a magnetic stirrerbar. This resulting mixture was sealed and degassed via vacuum evacuation and subsequent backfill with ethylene for three times. Then, N,N,N?,N?-tetramethylethylenediamine, TMEDA (60 muL, 2 equiv.)and N,N-diisopropylethylamine, DIPEA (70 muL, 2 equiv.) were subsequently added in this order. The solution was gently bubbled with ethylene balloon for approximately 30 seconds. The solution was then taken up into a 8 mL stainless steel syringe pre-purged with argon, and quickly assembled onto thestop-flow micro tubing, SFMT setup. Solution was pumped into the SFMT at 400 muL/min while maintaining approximately 1:1 gas-liquid slug flow at 250 PSI. Filled SFMT was then irradiated with blueLED (2 meter strip, 18 W) in a 100oC oil bath for 24 hours. The SFMT was wash with DCM (8 mL) and subjected to GC analysis (Figure S5). Then water (30 mL) was added to reaction mixture and extracted with DCM (10 mL) three times. Combined organic layer was successively wash with brine three timesand dried over Na2SO4 and concentrated under reduced pressure. The residue was then subjected to flash column chromatography to yield the product as a mixture of meso/dl isomers (which could not be separated by column chromatography).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Li, Jiesheng; Luo, Yixin; Cheo, Han Wen; Lan, Yu; Wu, Jie; Chem; vol. 5; 1; (2019); p. 192 – 203;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 847685-01-2, name is 4,5-Difluoro-2-iodoaniline, 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. Formula: C6H4F2IN

General procedure: Pd(PPh3)2Cl2 (28 mg, 0.04 mmol), CuI (17 mg, 0.09 mmol) and Et3N (3 mL) were added to a stirred solution of 2-iodaniline 3 (1 mmol) and ethynylaniline 4 (1.3 mmol) in MeCN (12 mL) at r.t. in an argon atmosphere. The reaction mixture was stirred at 60 C for 4 h and allowed to cool to r.t. Then, the mixture was diluted with CH2Cl2 (10 mL), poured into H2O (40 mL) and extracted with CH2Cl2 (3¡Á50 mL). The combined organic layers were washed with H2O (30 mL) and dried (MgSO4). Evaporation of the solvent in vacuo yielded crude product 2 and a small amount of 9 that were separated and purified by preparative TLC.

The synthetic route of 4,5-Difluoro-2-iodoaniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Politanskaya, Larisa V.; Shteingarts, Vitalij D.; Tretyakov, Evgeny V.; Journal of Fluorine Chemistry; vol. 188; (2016); p. 85 – 98;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 25252-00-0, The chemical industry reduces the impact on the environment during synthesis 25252-00-0, name is 2-Bromo-5-iodobenzoic acid, I believe this compound will play a more active role in future production and life.

General procedure: To a mixture of 2-bromo-5-iodo-benzoic acid (25 g, 76.5 mmol) in CH2Cl2 (80 ml) were added(COCl)2 (9 ml) and DMF (0.5 ml). The reaction mixture was stirred for 14 h at rt, and all volatile constituents were removed on rotary evaporator in vacuo. The residue was dissolved in CH2Cl2 (50 ml), and the resultant solution was cooled to 0 C. After addition of anisole (23 ml) to the mixture, AlCl3 (12.5 g) was added portionwise not to exceed 10 C. The solution was stirred at rt for overnight and then poured into ice. The organic phase was separated off, and aqueous phase was extracted with CH2Cl2 twice. After drying organic phases with MgSO4, the volatile compound was evaporated in vacuo.The crude product was purified with Biotage to afford (2-bromo-5-iodophenyl)(4-methoxyphenyl)methanone (25.8 g, 81%) as a light yellow solid. A solution of (2-bromo-5-iodophenyl)(4-methoxyphenyl)methanone(10 g, 24 mmol) and triethylsilane (TESH, 15.3 ml, 96 mmol) in a mixture of CH2Cl2 (30 ml) and CH3CN (60 ml) is cooled to 0 C. Then with stirring, BF3 etherate (5.0 ml, 36 mmol) was added slowly. The solution was stirred for 14 hr at rt. The solution was stirred for additional 3 hr at 50~60 C and then cooled to rt.The resulting solution was quenched with aqueous KOH solution (50 ml) and the aqueous layer was extracted with ethyl acetate. After solvent was evaporated, the residue was purified with column chromatography to produce 1-bromo-4-iodo-2-(4-methoxybenzyl)benzene (6.96 g, 72%) as colorless oil. To a solution of 1-bromo-4-iodo-2-(4-methoxybenzyl)benzene (7.5 g, 18.6 mmol) in CH2Cl2 (50 ml) at 0 C was added BBr3 in CH2Cl2 (1.0 M, 37.5 ml) dropwise, and the reaction solution was then stirred for 3 h at rt. The resulting solution was quenched with MeOH and the volatile constituents were removed on rotary evaporator. The residue was purified with Biotage to afford 4-(2-bromo-5-iodobenzyl)phenol (6.7 g, 92%) as a white solid. To a mixture of 4-(2-bromo-5-iodobenzyl)phenol (6.7 g, 17.2 mmol) and K2CO3 (9.5 g, 68.8 mmol) in CH3CN(50 ml) was added allylbromide (3.2 ml, 37 mmol). The reaction mixture was stirred for 24 hr at rt. After filteration of insoluble compounds, the filtrate was evaporated, and the residue was purified with Biotage to produce 2-(4-(allyloxy)benzyl)-1-bromo-4-iodobenzene (6.9 g, 95%) as colorless oil.

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, 2-Bromo-5-iodobenzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kang, Suk Youn; Kim, Min Ju; Lee, Jun Sung; Lee, Jinhwa; Bioorganic and Medicinal Chemistry Letters; vol. 21; 12; (2011); p. 3759 – 3763;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 63131-30-6, The chemical industry reduces the impact on the environment during synthesis 63131-30-6, name is Ethyl 3-(4-iodophenyl)-3-oxopropanoate, I believe this compound will play a more active role in future production and life.

Preparation of ethyl 3-(4-iodophenyl)-3-(phenylamino)acrylate 24[00332]To a solution of aniline (2.93g, 2.86ml, 31.4mmol) in EtOH (10ml), acetic acid (1.89g, 1.80ml, 31.4mmol) was added, followed by the addition of a solution of ethyl (4-iodobenzoyl) acetate in EtOH (10ml). The resulting solution was heated to reflux for at least 4 hours. EtOH was removed in vacuo, and the residue dissolved in DCM. The DCM solution was then washed with water, 5%HCl(aq.) and brine, and dried with Na2S04. The DCM was removed in vacuo to give the crude product as a yellow solid. The crude product was purified by columnchromatography eluting with 5% EtOAc in hexane to give the title product (1.06, 86%) as a pale yellow crystalline solid. 1H NMR (400 MHz, CDC13) delta 10.23 (s, 1H), 7.62 (d, J = 8.5 Hz, 2H), 7.17 – 7.02 (m, 5H), 6.94 (t, J = 6.9 Hz, 1H), 6.66 (d, J = 7.5 Hz, 2H), 4.97 (s, 1H), 4.20 (q, J = 7.1 Hz, 2H), 1.31 (t, J = 7.1 Hz, 3H).

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, Ethyl 3-(4-iodophenyl)-3-oxopropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LIVERPOOL SCHOOL OF TROPICAL MEDICINE; O’NEILL, Paul; BIAGINI, Giancarlo; WARD, Stephen A.; BERRY, Neil Graham; NIXON, Gemma; AMEWU, Richard K.; PIDATHALA, Chandrakala; HONG, Weiqian David; GIBBONS, Peter; LEUNG, Suet Ching; PACOREL, Benedicte; SHARMA, Raman; LAWRENSON, Alexandre S.; SHONE, Alison E.; SRIVASTAVA, Abhishek; WARMAN, Ashley J.; WO2012/69856; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 619-58-9, name is 4-Iodobenzoic acid, A new synthetic method of this compound is introduced below., SDS of cas: 619-58-9

Step A — Preparation of p-iodobenzyl alcohol To a stirred solution of p-iodobenzoic acid (5 mmole) in a dry tetrahydrofuran (20 ml) at -70 is added a suspension of lithium aluminum hydride (10 mmole) in tetrahydrofuran (10 ml). The mixture is allowed to warm to 0 and stirred at 0 for 2 hours. The reaction mixture is then poured into a dilute hydrochloric acid — ice mixture and extracted with ether. The ether extract is washed with dilute bicarbonate solution, washed, dried over sodium sulfate and concentrated to dryness. Chromatography of the residue on a silica gel gives p-iodobenzyl alcohol.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Merck & Co., Inc.; US4064236; (1977); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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 624-75-9 as follows. Safety of 2-Iodoacetonitrile

General procedure: Individual solutions of secondary N-alpha-trimethylsilylmethyl-N-benzylamines19 (5mmol) in acetonitrile (100mL) containing K2CO3 (10mmol) and 2-iodoacetonitrile (4.5mmol) were stirred for 12hat room temperature and concentrated in vacuo to give residues that were partitioned between water and CH2Cl2. The CH2Cl2 layers were dried and concentrated in vacuo to afford residues that were subjected to silica gel column chromatography (EtOAc/hexane=1: 15 – 1: 30) to yield corresponding alpha-aminonitiriles 11a18 (91%), 11b (74%), 11c (78%), 11d (85%), 11e (75%), 11f (75%), 11g (74%), 11h (75%), 11i (78%), 11j (78%) and 11k (66%).

According to the analysis of related databases, 624-75-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lim, Suk Hyun; Cho, Dae Won; Choi, Jungkweon; An, Hyunjun; Shim, Jun Ho; Mariano, Patrick S.; Tetrahedron; vol. 73; 44; (2017); p. 6249 – 6261;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 75581-11-2, 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 75581-11-2 as follows.

General procedure: A DMF solution (8mL) of the o-substituted aryl iodide (0.36mmol), the o-bromobenzyl alcohol (0.36mmol) and norbornene (34mg, 0.36mmol) was added under nitrogen to a Schlenck-type flask, containing Pd(OAc)2 (4mg, 0.018mmol), the phosphine (0.036mmol), when required, and K2CO3 (124mg, 0.90mmol) or CsOPiv (211mg, 0.90). The reaction mixture was stirred at 105C for 24h. After cooling to room temperature the organic layer was diluted with EtOAc (20mL), washed twice with water (20mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the resulting residue was purified by flash chromatography on silica gel using mixtures of hexane-EtOAc as eluent.

According to the analysis of related databases, 75581-11-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Della Ca, Nicola; Fontana, Marco; Xu, Di; Cremaschi, Mirko; Lucentini, Riccardo; Zhou, Zhi-Ming; Catellani, Marta; Motti, Elena; Tetrahedron; vol. 71; 37; (2015); p. 6389 – 6401;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 791642-68-7, name is 4-Bromo-1-iodo-2-methoxybenzene, A new synthetic method of this compound is introduced below., Safety of 4-Bromo-1-iodo-2-methoxybenzene

To a solution of 4-bromo-1-iodo-2-methoxybenzene (1.634 g, 5.221 mmol) in dry acetonitrile (20 mL) Cul (49.7 mg, 0.261 mmol) and Pd(Ph3P)2Cl2 (183.2 mg, 0.261 mmol) were added under Argon atmosphere and the mixture was degassed and backfilled with Argon for three times. TEA (0.728 mL, 5.221 mmol) and (ethynyl)trimethylsilane(l .48 mL, 1.03 g, 10.442 mmol) were added with a syringe and the reaction mixture, that darkened within 10 min, was stirred at room temperature for 1 h. The solvent was removed under vacuum and the residue was taken up with EtOAc (100 mL), washed with brine (3 x 20 mL), water (20 mL), dried over sodium sulphate and evaporated to dryness. The crude was purified by chromatography on silica gel (petroleum ether/diethyl ether 9/1) to yield the title compound as an orange solid (1.426 g, 96.5%). 1H NMR (400 MHz, DMSO-cie) delta ppm 0.21 (s, 9 H) 3.83 (s, 3 H) 7.11 (dd, J=8.18, 1.83 Hz, 1 H) 7.26 (d, J=1.83 Hz, 1 H) 7.31 (d, J=8.06 Hz, 1 H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; BRASCA, Maria, Gabriella; BERTRAND, Jay, Aaron; GNOCCHI, Paola; MOTTO, Ilaria; NESI, Marcella; PANZERI, Achille; VIANELLO, Paola; WO2013/14039; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com