Month: September 2021

Adding a certain compound to certain chemical reactions, such as: 181765-86-6, name is Methyl 5-bromo-2-iodobenzoate, belongs to iodides-buliding-blocks compound, 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 181765-86-6, COA of Formula: C8H6BrIO2

A 500 mL round bottom flask reactor was charged with methyl 5-bromo-2-iodobenzoate (1.7g, 0.15mmol) and potassium carbonate (20.2g, 146.7mmol) were added to a toluene solution (25.0g, 73mmol), 4-dibenzofuranboronic acid (18.7g, 88mmol) 125 mL of tetrahydrofuran, and 50 mL of water. The temperature of the reactor was raised to 80 C and stirred for 10 hours. When the reaction was completed, the temperature of the reactor was lowered to room temperature, extracted with ethyl acetate, and the organic layer was separated. The organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain Intermediate 1-a (75.0 g, 60.1%).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; SFC Co.,Ltd.; Cha, Sun Wook; Sin, Yoo Na; Lim, Jae Geon; Park, Jin Joo; Park, Sang Woo; Kim, Ji Hwan; Yoo, Jung Ho; Park, Young Hwan; (53 pag.)KR2017/86011; (2017); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 610-97-9, A common heterocyclic compound, 610-97-9, name is Methyl 2-iodobenzoate, molecular formula is C8H7IO2, 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: A 50mL round-bottomed flask equipped with a gas inlet tube, a reflux condenser, and a magnetic stirring bar was charged with MCM-41-S-PdCl2 (173mg, 0.05 mmol Pd), aryl halide (5.0 mmol) and HCOONa (7.5 mmol). The flask was flushed with carbon monoxide. DMF (5 mL) was added by syringe and a slow stream of CO was passed into the suspension. The mixture was vigorously stirred at 100-110C for 4-24h, cooled to room temperature, and diluted with diethyl ether (50 mL). The palladium catalyst was separated from the mixture by filtration, washed with distilled water (2×10 mL), ethanol (2×10 mL) and ether (2×10 mL) and reused in the next run. The ethereal solution was washed with water (3×20mL) and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane-ethyl acetate=10:1). (0008) All formylation products were characterized by comparison of their spectra and physical data with authentic samples. IR spectra were determined on a Perkin-Elmer 683 instrument. 1H NMR (400MHz) and 13C NMR (100MHz) spectra were recorded on a Bruker Avance 400MHz spectrometer with TMS as an internal standard and CDCl3 as solvent.

The synthetic route of 610-97-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hao, Wenyan; Ding, Guodong; Cai, Mingzhong; Catalysis Communications; vol. 51; (2014); p. 53 – 57;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 19718-49-1, A common heterocyclic compound, 19718-49-1, name is Methyl 4-amino-3-iodobenzoate, molecular formula is C8H8INO2, 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 solution of methyl 4-amino-3-iodobenzoate (1.0 g, 3.61 mmol) and triethylamine (1.003 mL, 7.22 mmol) in dichloromethane (20 mL) was added dropwise to a cooled (0 0C) solution of trifiuoroacetic anhydride (1.275 mL, 9.02 mmol) in dichloromethane (5 mL). The cooling was removed, the mixture was stirred at room temperature for 3 hours, poured into ice-water and extracted with dichloromethane. The organic phase was dried over sodium sulfate and the solvent was evaporated. Purification by column chromatography, using heptane/ethyl acetate (4:1) as the eluent, gave 1.23 g (91% yield) of the title compound. 1H NMR (500 MHz, CD3OD) delta ppm 8.54 (d, 1 H) 8.07 (dd, 1 H) 7.57 (d, 1 H) 3.93 (s, 3 H); MS (ESI) m/z 372 [M-I]”.

The synthetic route of 19718-49-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2009/64251; (2009); A1;,
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. 19718-49-1, name is Methyl 4-amino-3-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 4-amino-3-iodobenzoate

A suspension of methyl 4-amino-3-iodobenzoate (500 mg, 1.81 mmol), 1 -methyl -4-(4, 4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrazole (563 mg, 2.71 mmol), Pd(dppf)Cl2 (132 mg, 0.18 mmol) and Cs2C03 (1177 mg, 3.61 mmol) in Dioxane/H20 (10 mL/2 mL) was stirred at 90C for 8h under Nitrogen. The mixture was then diluted with H20 (30 mL) and extracted with DCM (30 mL*2). The combined organic phases were concentrated in vacuo and the residue was purified by flash chromatography on silica gel (Petroleum Ether/Ethyl Acetate = 1/1) to afford methyl 4- amino-3-(l-methyl-lH-pyrazol-4-yl)benzoate (417 mg, 100%) as a brown solid. MS Calcd.: 231, MS Found: 232 ([M+H]+).

According to the analysis of related databases, 19718-49-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KINNATE BIOPHARMA INC.; KANOUNI, Toufike; ARNOLD, Lee D.; KALDOR, Stephen W.; MURPHY, Eric A.; TYHONAS, John; (0 pag.)WO2020/6497; (2020); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 103440-54-6,Some common heterocyclic compound, 103440-54-6, name is Methyl 5-iodo-2-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.

Preparation 37 Methyl 2-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzoate To a solution of methyl 5-iodo-2-methylbenzoate (Preparation 42, 69 g, 0.25 mol) in DMF (800 mL) was added bispinacolatodiboron (100 g, 0.40 mol) and potassium acetate (92 g, 0.93 mol) followed by degassing with nitrogen. [1 ,1 ‘- bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (6 g) was added and the reaction heated to 100C for 18 hours. The reaction was cooled and filtered through celite, washing through with EtOAc (3 x 1 L). The filtrates were combined, washed with brine (3 x 500 mL), dried over Na2S04 and concentrated in vacuo. The residue was washed with petroleum ether (2 x 500 mL), filtered and dried to afford the title compound as a yellow powder (60 g, 87%) that was taken directly on to the next step.

The synthetic route of 103440-54-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; OWEN, Robert Mckenzie; PRYDE, David Cameron; TAKEUCHI, Mifune; WATSON, Christine Anne Louise; WO2015/189744; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 40400-15-5, A common heterocyclic compound, 40400-15-5, name is 2-(2-Iodophenyl)acetonitrile, molecular formula is C8H6IN, 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.

30.0 g (0.123 mol) of 2-iodophenylacetonitrile, 66.0 g (0.370 mol) of diphenylacetylene, 11.3 g (0.0123 mol) of tris(dibenzylideneacetone)dipalladium, 30.0 g (0.123 mol) of triethylamine, 210 mL of dimethylformamide, and 30 mL of water were stirred in a round-bottom flask at 130 C. for 48 h. After completion of the reaction, the organic layer was extracted, purified by column chromatography, and dried to afford 28 g of Intermediate 11-a (yield 77%).

The synthetic route of 40400-15-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SFC CO., LTD.; LEE, Se-jin; LEE, Bong-Hyang; YU, Taejung; CHOI, Yeongtae; LEE, Dajung; (58 pag.)US2019/140177; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

627-32-7, name is 3-Iodo-1-propanol, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C3H7IO

The reaction of phenoxazine (500 mg, 2.729 mmol) and NaH (60% dispersion in mineral oil, 136.8 mg, 4.094 mmol) in distilled DMF (10 mL) with 3-bromo-1-propanol (621 mg, 4.094 mmol) ), as described above, gave compound 14 (480.7 mg, 1.992 mmol, 73 %) as dark navy oil.: Rf = 0.33 (n-hexane/EtOAc = 1:1); IR (neat, cm-1) 3365, 3065, 2947, 1592, 1487, 1380, 1272, 1130, 1044; 1H NMR (400 MHz, CD3OD) delta 6.72~6.76 (m, 2H), 6.51~6.61 (m, 6H), 3.66 (t, 2H, J = 5.6 Hz), 3.60 (t, 2H, J = 7.6 Hz), 1.80 (m, 2H); 13C NMR (100 MHz, CD3OD) delta 145.0, 133.4, 123.7, 120.6, 115.0, 111.6, 59.2, 40.5, 27.7; MS (FAB) m/z 241.1 (M+).

The synthetic route of 627-32-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gim, Hyo Jin; Li, Hua; Lee, Eun; Ryu, Jae-Ha; Jeon, Raok; Bioorganic and Medicinal Chemistry Letters; vol. 23; 2; (2013); p. 513 – 517;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 116632-39-4, name is 5-Bromo-2-iodotoluene, molecular formula is C7H6BrI, 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. Recommanded Product: 116632-39-4

Apparatus set-up: (0305) A 5 L 3 -necked round-bottomed flask, equipped with a mechanical overhead stirrer, reflux condenser, nitrogen inlet and exhaust. (0306) Experimental Procedure: (0307) Intermediate 3 (128 g, 0.435 mol) and intermediate 4 (128.8 g, 0.435 mol) were taken in toluene (1 L) and ethanol (1 L). (0308) Sodium carbonate solution (161.3 g, 1.522 mol, dissolved in 500 mL of water) was added. (0309) The reaction mixture was degassed with nitrogen for an hour. (0310) PdCl2 (PPh3)2 (15.2 g, 0.021 mol) was added and heated at 80 C for 18 h. (0311) After completion of the reaction, the mixture was filtered through a Florosil-silica plug and concentrated. (0312) The residue was dissolved in ethyl acetate (2 L), washed with water (1 L), brine (1 L), dried over sodium sulphate and concentrated. (0313) The crude product (159 g) was purified by silica column chromatography using 5 to 6 % ethyl acetate in hexane as an eluent to get 65 g of Intermediate B with 81 % HPLC purity. It was again purified by reverse phase column chromatography (in 5 g per run) using water/ acetonitrile as an eluent to get 35.6 g of Intermediate B. (0314) The material was dissolved in dichloromethane (500 mL), heated to 45 C, filtered the hot solution and concentrated to get 35 g of Intermediate B with 99.64 % HPLC purity as viscous oil. (0315) ^-NMR (400 MHz, COCh): delta [ppm] 2.29 (s, 3H), 7.19 (d, = 8.0 Hz, 1H), 7.37 – 7.42 (m, 3H), 7.47 – 7.52 (m, 2H), 7.61 (d, / = 8.4 Hz, 2H), 7.86 (s, 1H), 7.96 (d, = 7.6 Hz, (0316) 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 116632-39-4, its application will become more common.

Reference:
Patent; CAMBRIDGE DISPLAY TECHNOLOGY LIMITED; SUMITOMO CHEMICAL CO., LTD; HUMPHRIES, Martin; TARRAN, William; KAMTEKAR, Kiran; STACKHOUSE, Philip; LEE, James; (76 pag.)WO2017/153731; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 75581-11-2, name is 4-Iodo-1-methoxy-2-methylbenzene, belongs to iodides-buliding-blocks compound, 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 75581-11-2, COA of Formula: C8H9IO

To a stirring solution of aryl iodide S12 (5.0 g, 20 mmol, 1 .0 equiv), PdCI2(PPh3)2 (0.28 g, 0.40 mmol, 2 mol%), and Cul (0.15 g, 0.79 mmol, 4 mol%) in 50 ml_ triethylamine under N2 atmosphere at rt was added TMS-acetylene (2.4 g, 24 mmol, 1 .2 equiv) dropwise. The resulting yellow suspension was stirred overnight (approx. 17 h) under N2 atmosphere at rt. The reaction mixture was filtered through a pad of celite, and the filtrate was concentrated in vacuo. The crude oil was dissolved in hexanes, and then passed through a pad of silica using 95% hexanes: 5% ethylacetate as the eluent. The resulting solution was dried over anhydrous Na2S04, filtered through a coarse fritted glass funnel, and the filtrate was concentrated in vacuo to afford 4.1 g of compound alkyne 28 as a yellow solid (93%).

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, 4-Iodo-1-methoxy-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TRUSTEES OF DARTMOUTH COLLEGE; MICALIZIO, Glenn C.; EASTMAN, Alan; (149 pag.)WO2019/35061; (2019); 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. 89459-38-1, name is 2-Iodo-4-nitrobenzoic acid, A new synthetic method of this compound is introduced below., Quality Control of 2-Iodo-4-nitrobenzoic acid

Reference Example 82 2-Iodo-N-methoxy-N-methyl-4-nitrobenzamide An aqueous solution (8 ml) of sodium nitrite (2.27 g) was added to an aqueous solution (40 ml) of 4-nitroanthranilic acid (5.00 g) under ice-cooling. Subsequently, an aqueous solution (6 ml) of potassium iodide (5.47 g) was added to the mixture, followed by stirring at room temperature for 20 minutes, and then the mixture was heated to 75C, followed by further stirring for 10 minutes. After completion of the reaction, sodium hydrogen sulfite was added to the mixture under ice-cooling, and the mixture was extracted with dichloromethane-methanol (10:1, v/v). The organic layer was washed with water and saturated brine and dried over sodium sulfate. The residue obtained by evaporating the solvent was again dissolved in water and the same operation described in the above was repeated, and the thus obtained residue was used in the subsequent reaction without purification. The above-described residue was dissolved in dichloromethane, and N,O-dimethylhydroxylamine hydrochloride (3.21 g), HOBt (4.45 g), EDC-HCl (6.31 g) and N-methylmorpholine (3.6 ml) were added to the solution at 0C, followed by stirring overnight at room temperature. To the reaction solution was adde a saturated aqueous sodium bicarbonate solution, extracted with dichloromethane, washed with 1 N hydrochloric acid, water and saturated brine and dried over sodium sulfate. The solvent was evaporated, the thus obtained residue was purified by silica gel column chromatography, and the fraction obtained from the elude of n-hexane:ethyl acetate = 2:1 was concentrated under reduced pressure to obtain the title compound (6.57 g) as a colorless solid. 1H-NMR (400 MHz, CDCl3) delta: 3.41 (3H, s), 3.49 (3H, s), 7.44 (1H, d, J=8.5 Hz), 8.26 (1H, d, J=2.0 and 8.5 Hz), 8.67 (1H, d, J=2.0 Hz).

The synthetic route of 89459-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1612204; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com