Category: iodides-buliding-blocks

Electric Literature of 136618-42-3, A common heterocyclic compound, 136618-42-3, name is Benzyl 4-iodobenzoate, molecular formula is C14H11IO2, 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.

Intermediate 8: Phenvlmethvl 4-(4-amino-6-methvl-1H-indazol-1-vl)benzoate; 6-Methyl-1 W-indazol-4-amine (5.48g, 37.3mmol), copper (I) iodide (71 mg, 0.37mmol), trans-1 ,2-cyclohexanediamine (420mg, 0.37mmol) and tripotassium phosphate (16.6g, 78.3mmol) were added to a solution of phenylmethyl 4-iodobenzoate (12.61g, 37.3mmol) in 1 ,4-dioxane (2OmL). More 1 ,4-dioxane (3OmL) was added and the mixture heated under reflux for 3 hours 15 min and then allowed to gradually cool to room temperature and partitioned between water and ethyl acetate. The aqueous phase was extracted once more with ethyl acetate and the combined organic extracts were washed with brine and dried and evaporated to give a brown solid (13.58g). This crude product was combined with material (0.66g) from a similar reaction and purified by column chromatography on silica gel (Merck 7734, 50OmL) eluting initially with 10% and finally with 20% ethyl acetate in dichloromethane. Evaporation of product containing fractions gave a brown-yellow solid (5.12g) which was dissolved in ethyl acetate (4OmL) at 60 and warm cyclohexane (7OmL) was added. The mixture was then cooled in ice and the precipitate was collected by filtration, washed with cyclohexane:ethyl acetate (4:1 , 4OmL) and dried to give the title compound as a beige solid (4.29g). LCMS (System A): tRET = 3.77 min; MNH4+ = 358

The synthetic route of 136618-42-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/50243; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

264927-52-8, name is 2-Chloro-4-fluoro-5-iodobenzoic acid, 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. HPLC of Formula: C7H3ClFIO2

To a stirred solution of compound 3 (2.200 g, 7.33 mmol) in anhydrous DMF (20 mL) was added K2CO3 (0.846 g, 8.06 mmol) and isopropyl iodide (1.870 g, 10.99 mmol) in sequence at room temperature. The resulting mixture was stirred at the same temperature for 6 h and saturated NH4Cl(aq) (10 mL) was added to quench the reaction. The aqueous layer was separated and extracted with EtOAc (20*3 mL). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated to give the crude residue, which was purified by flash chromatography on silica gel with EtOAc/n-hexane (1:19) to afford compound 5 (2.407 g, 96% yield) as white solid. Mp 43-44 C; IR (neat): 1732, 1714, 1585, 1558, 1463, 1371, 1284, 1271, 1255 cm-1; 1H NMR (500 MHz, CDCl3): delta=8.23 (d, J=6.5 Hz, 1H), 7.19 (dd, J=7.5, 1.0 Hz, 1H), 5.28 (septet, J=6.0 Hz, 1H), 1.41 (d, J=6.0 Hz, 6H); 13C NMR (125 MHz, CDCl3): delta=163.1, 163.0 (d, J=252.5 Hz), 141.9 (d, J=2.5 Hz), 135.5 (d, J=10.0 Hz), 128.4 (d, J=3.7 Hz), 118.4 (d, J=26.2 Hz), 78.6 (d, J=26.2 Hz), 69.9, 21.8 (2*CH3); 19F NMR (470 MHz, CDCl3): delta=-89.5; HRMS (EI) m/z [M]+ calcd for C10H9ClFIO2: 341.9320; found: 341.9321.

The synthetic route of 264927-52-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hsieh, Min-Tsang; Lin, Hui-Chang; Kuo, Sheng-Chu; Tetrahedron; vol. 72; 39; (2016); p. 5880 – 5885;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 773855-64-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 773855-64-4 name is 1-Fluoro-4-iodo-2-methoxybenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Dissolve l-fluoro-4-iodo-2-methoxybenzene, (prepared as described in PREPARATION 47), (1. 0 g, 4. 0 mmol) in triethylamine (15 mL, 108 mmol) and add 3- ethynyl-5-methoxypyridine, (prepared as described in PREPARATION 10), (500 mg, 3. 8 mmol) followed by bis (triphenylphosphine) palladium (II) dichloride (100 mg, 0. 14 mmol) and copper (I) iodide (60 mg, 0. 32 mmol). Stir for 18 h at room temperature, concentrate and purify by silica gel chromatography, eluting with 3 : 1 hexanes : ethyl acetate. Further purify on silica gel, eluting with 9 : 1 dichloromethane : ethyl acetate, to give the title compound as a white solid (650 mg, 65%). 1HNMR (300 MHz, CDC13) 6 3. 88 (s, 3H), 3. 92 (s, 3H), 6. 98-7. 15 (m, 3H), 7. 29-7. 31 (m, 1H), 8. 27 (d, J = 2. 8 Hz, 1H), 8. 37 (d, J = 1. 5 Hz, 1H) ; MS (APCI) : m/z= 258 [M+H] +.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Fluoro-4-iodo-2-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/94822; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 914106-26-6, 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. 914106-26-6, name is 4-Chloro-3-iodobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 4-chloro-3-iodobenzonitrile (0.80 g, 3.0 mmol) in THF (16 mL) under nitrogen was added BH3-THF (1M in THF, 4.8 mL, 4.8 mmol). After stirring for 30 minutes at room temperature, the reaction mixture was heated to reflux for 8 hours. The reaction mixture was cooled to 0C, and a 2M aqueous HCI solution (4.5 mL) was added slowly. The reaction mixture was allowed to warm to room temperature, and heated to reflux for 2.5 hours. After cooling to room temperature, the mixture was concentrated in vacuo to yield crude Intermediate 6A which was used without purification. 1H NMR (CD3OD) delta 8.07 (d, 1H), 7.58 (d, 1H), 7.48 (m, 1H), 4.10 (s, 2H).

The chemical industry reduces the impact on the environment during synthesis 4-Chloro-3-iodobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; VENENUM BIODESIGN LLC; HUANG, Chia-Yu; SHI, Dongchuan; KULTGEN, Steven G.; MCGUINNESS, Brian F; LETOURNEAU, Jeffrey J.; COLE, Andrew G.; BEASLEY, James R.; (358 pag.)WO2018/5801; (2018); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 141738-80-9, name is 3-Chloro-4-iodobenzotrifluoride, 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: C7H3ClF3I

In 2-chloro-1-iodo-4 – (trifluoromethyl) benzene (100 mg, 0 . 33mmol), acrylic acid (0.029 ml, 0 . 42mmol) palladium (II) and acetic acid (3.7 mg, 0 . 016mmol) the acetonitrile solution (1.0 ml) is added triethylamine (0.11 ml, 0 . 82mmol), for the microwave irradiation, for 110 C stirring 30 minutes. The reaction mixture after cooling to room temperature, filtered using silicon, the minute filters insolubles. To the filtrate 1N dilute acid solution, after extraction with ethyl acetate, the organic layer with anhydrous magnesium sulfate drying. After the desiccant filter and the obtained concentrated under reduced pressure the residue by silica gel column chromatography (methanol/dichloromethane) refining, to obtain the title compound (75 mg, 92%).

The synthetic route of 3-Chloro-4-iodobenzotrifluoride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHUGAI SEIYAKU KABUSHIKI KAISHA; MURATA, TAKESHI; HARA, SOUSUKE; NIIZUMA, SATOSHI; HADA, KIHITO; KAWADA, HATSUO; SAKAITANI, MASAHIRO; SHIMADA, HIDEAKI; NAKANISHI, YOSHITO; (453 pag.)TW2016/5805; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 89976-43-2, name is 4-Iodo-N-methylbenzamide, 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 89976-43-2, Computed Properties of C8H8INO

2e) N-Methyl-4-trimethylsilanylethynyl-benzamide A mixture of 4-iodo-N-methylbenzenamide (26.1 g, 0.1 mole), 2.5 g of PdCl2(PPh3)2 (3,5%) and 1.6 g Cul (8%) in 200 ml of toluene was stirred for 30 min under argon. Than 1-ethynyl(trimethyl)silane (10 g, 0.102 mole) and Et3N (40.4 g, 0.4 mole) was added. This mixture was stirred for 2-3 hours under argon at r.t. Sub products were filtered off. The solvent was evaporated product was purified by flash chromatography with CHCl3. Chloroform was evaporated and product was crystallized from hexane. Yield – 17.65 g (75.7%)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Iodo-N-methylbenzamide, and friends who are interested can also refer to it.

Reference:
Patent; Bayer Schering Pharma Aktiengesellschaft; EP2020404; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 3824-21-3, 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. 3824-21-3, name is 2-Fluoro-4-iodo-1-methoxybenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-fluoro-6-iodo-3-methoxybenzoic acidInto an 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 2-fluoro-4-iodo-1-methoxybenzene (5.00 g, 19.84 mmol, 1.00 equiv) in tetrahydrofuran (40 mL) with stirring at -78 C. This was followed by the addition of LDA (1.8 N, 11 mL, 1.10 equiv, in THF solution) dropwise at -78 C. The resulted solution was stirred for 1h at -78 C. Carbon dioxide was bubbled into the reaction solution with stirring. The reaction mixture was warmed up to room temperature and stirred overnight. Then it was concentrated under vacuum and diluted with sodium hydroxide aqueous solution (30 mL, 4N). The mixture was extracted with 30 mL of ethyl acetate. The pH value of the aqueous phase was adjusted to 2.0 with 2N hydrochloride aqueous solution. The resulted solution was extracted with 3×50 mL of ethyl acetate. The organic layers were combined and concentrated under vacuum. This resulted in 3.10 g (53%) of 2-fluoro-6-iodo-3-methoxybenzoic acid as light yellow solid. LC-MS (ESI) m/z: calculated for C8H6FIO3: 296. found: 295[M-1]-.

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-Fluoro-4-iodo-1-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Global Blood Therapeutics, Inc.; Li, Zhe; Xu, Qing; Yu, Chul; Yee, Calvin; Gwaltney,, II, Stephen L.; Metcalf, Brian W.; Richards, Steven; Lardy, Matthew A.; Setti, Lina; Sham, Hing; US2015/315198; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 845866-78-6, 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. 845866-78-6, name is 1-Bromo-3-iodo-5-(trifluoromethoxy)benzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A 5 mL microwave vial was charged with l-bromo-3-iodo-5-(trifluoromethoxy)benzene(98 mg, 0.27 mmol), (6-methylpyridin-3-yl)methanamine (50 mg, 0.41 mmol), molybdenum hexacarbonyl (160 mg, 0.61 mmol), palladium acetate (8 mg, 0.036 mmol), l,8-diazabicyclo[5.4.0]undec- 7-ene (120 mg, 0.79 mmol), and 1,4-dioxane (2 mL). The vial was sealed under nitrogen and the reaction was subjected to microwave irradiation at 120 0C for 20 minutes. After cooling, the mixture was purified via flash chromatography to afford the desired product as a white solid. LC-MS: 391.2 [M+l]+; 1H NMR (CDCl3, 400 MHz): 8.43 (d, J = 2.1 Hz, IH), 7.85 (t, J = 1.5 Hz, IH), 7.63-7.61 (m, 2H), 7.52 (s, IH), 7.16 (d, J = 8.0 Hz, IH), 6.74 (br, IH), 4.60 (d, J = 5.8 Hz, 2H), 2.55 (s, 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, 1-Bromo-3-iodo-5-(trifluoromethoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RENOVIS, INC.; WO2009/110985; (2009); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 13101-40-1, 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. 13101-40-1, name is 1-Bromo-3-chloro-5-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Potassium carbonate (as 2 M aqueous solution, 2 eq.) was degassed with nitrogen for 30 min. Dioxane (976 ml) was also degassed with nitrogen for 30 min. The THF flask was then charged with corresponding 9-phenanthreneboronic add (10 mmol, 1.32 eq.), previously synthesized formula 6 intermediate (78 g, 1 eq.) and tetrakis(triphenylphosphin)palladium(o) (0.035 eq.) under a positive nitrogen pressure. The degassed potassium carbonate solution was added, nitrogen purged reflux condenser was attached to the flask and a reaction mixture heated to 65 C with stirring for 48 h. The mixture was allowed to cool down to the room temperature, dioxane was evaporated. Extraction with 1.75 L chloroform was performed. After washing the organic layer with 5 x 250 mL water, it was dried over MgSOq and filtered over silicagel layer. Evaporation almost to dryness followed by hexane addition provided a precipitate that was still colored. Further washing with Na2S20s sat. aqueous solution afforded 49.2g (54%) product, m/z 366, 368 [M]+

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, 1-Bromo-3-chloro-5-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVALED GMBH; SCHULZE, Benjamin; CARDINALI, Francois; SCHOLZ, Johannes; (74 pag.)WO2019/201621; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route 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.

Copper(I) iodide (69.4 mg, 0.364 mmol), 2-phenylphenol (93.0 mg, 0.546 mmol) and cesium carbonate (1.78 g, 5.46 mmol) were added to a dry flask under nitrogen. Ethyl malonate (1.11 mL, 7.29 mmol) was added to the mixture, followed by l-chloro-2,5-difluoro-4- iodobenzene (1.00 g, 3.64 mmol) in tetrahydrofuran (3.64 mL, 44.9 mmol). The reaction mixture was sealed and heated to 90C. After 12 hours, the reaction mixture was allowed to cool to room temperature and then diluted with saturated NH4Cl and EtOAc. The organic layer was separated, dried and filtered through Celite. The brown oil was purified via silica gel chromatography (0-30% EtOAc-hexane) to give diethyl 2-(4-chloro-2,5-difluorophenyl)malonate (0.65 g, 58%). 1H NMR (400 MHz, CDCl3) delta 7.37 (dd, J = 6.3, 9.3, IH), 7.17 (dd, J = 6.1, 8.9, IH), 4.91 (s, IH), 4.33 – 4.14 (m, 4H), 1.28 (t, J = 7.2, 6H).

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

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; WO2009/6567; (2009); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com