Author: Jessica.F

These common heterocyclic compound, 13421-00-6, name is 5-Chloro-2-iodobenzoic acid, 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. HPLC of Formula: C7H4ClIO2

In a round-bottomed flask equipped with an overhead magnetic stirrer, reflux condenser, and nitrogen inlet were added 5-chloro-2-iodobenzoic acid (1 .15 g, 4.07 mmol), copper iodide (0.04 g, 0.2 mmol), and CS2CO3 (2.65 g, 8.14 mmol). To these solids were added dioxane (6 mL), water (0.05 mL), then 1 H-1 ,2,3-triazole (0.47 mL, 8.14 mmol), and finally trans-1 ,2-dimethylcyclohexane-1 ,2-diamine (0.3 mL, 0.81 mmol). The mixture was then warmed to 100 C for 4 hrs. Then the mixture was cooled and then MTBE and of water were added. After vigorous mixing, the layers were separated and the bottom aqueous layer was acidified to pH 2 with 6N HCI. The aqueous was then extracted twice with EtOAc. The combined organic layers were dried, filtered, and concentrated. The oil was stirred overnight in EtOAc (8 mL) and the resulting precipitate was removed by filtration affording a first crop of wanted product(100 mg). The mother-liquors were concentrated and purified by FC on S1O2 column (eluting from DCM to DCM : MeOH: 90: 10) to afford a second batch of the desired product that was mixed with the former to afford 5-chloro-2-(2H-1 ,2,3-triazol-2- yl)benzoic acid (p120, 620 mg, y=68%). MS (mlz): 223.9 [MH]+

The synthetic route of 5-Chloro-2-iodobenzoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHRONOS THERAPEUTICS LIMITED; MICHELI, Fabrizio; BERTANI, Barbara; GIBSON, Karl Richard; DI FABIO, Romano; RAVEGLIA, Luca; ZANALETTI, Riccardo; CREMONESI, Susanna; POZZAN, Alfonso; SEMERARO, Teresa; TARSI, Luca; LUKER, Timothy Jon; (275 pag.)WO2019/43407; (2019); A1;,
Iodide – Wikipedia,
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Application of 3032-81-3, These common heterocyclic compound, 3032-81-3, name is 1,3-Dichloro-5-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.

EXAMPLE 26 1-(3,5-Dichlorophenyl)-3-methyl-1-butyn-3-ol A mixture of 25.5 g (0.094 mole) of 3,5-dichloroiodobenzene, 550 ml dry triethylamine, 12 g (0.14 mole) of 2-methyl-2-hydroxy-3-butyne, 0.42 g (0.0019 mole) palladium (II) acetate, and 1 g (0.0038 mole) of triphenylphosphine was heated to reflux under nitrogen for four hours. The resulting mixture was cooled, diluted with ether and washed with two 500-ml portions of 3N hydrochloric acid. The ether layer was separated, dried over anhydrous magnesium sulfate, and evaporated in vacuo to yield the crude product as an oily residue. The purified product was obtained by distillation to yield 7.95 g, bp 115°-125° C./0.0001 mm.

The synthetic route of 3032-81-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; McNeilab, Inc.; US4661635; (1987); A;,
Iodide – Wikipedia,
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Electric Literature of 624-76-0, These common heterocyclic compound, 624-76-0, name is 2-Iodoethanol, 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: Conc. H2SO4 (0.3 equiv.) was added to 9-(4-methoxyphenyl)fluoren-9-ol (13) (1.0 equiv.) in toluene and warmed up to 60 C for 15 min. After cooling the solution to rt the corresponding hydroxyl alkyl halide (1.5 equiv) or the alkyldiol (2.0 equiv.) was added. The reaction mixture was stirred at rt for the given time and then partitioned between water and toluene. The organic phase was dried over MgSO4, filtered, and concentrated to dryness. The crude product was then purified by CC (iso-hexane/EtOAc = 9.5:0.5). 5.1.1.1 9-(2-Iodoethoxy)-9-(4-methoxyphenyl)-9H-fluorene (21) According to GP1: 9-(4-methoxyphenyl)fluoren-9-ol (13) [21] (1.4 g, 4.8 mmol), toluene (12 mL), conc. H2SO4 (147 mg, 1.50 mmol, 80.0 muL), 2-iodoethanol (14) (1.26 g, 7.35 mmol, 0.573 mL), 20 h. Yield: 2.0 g (92%); colourless solid, m.p. 96-98 C; TLC: Rf = 0.24 (iso-hexane/EtOAc = 9.5/0.5); IR (KBr): 3035, 2931, 2903, 2841, 2044, 1951, 1918, 1605, 1580, 1508, 1447, 1302, 1252, 1184, 1169, 1107, 1031, 993 cm-1; 1H NMR (CDCl3): delta = 3.15-3.20 (m, 2 H, CH2O), 3.20-3.24 (m, 2 H, ICH2), 3.75 (s, 3 H, CH3), 6.76-6.81 (m, 2 H, Har), 7.26 (td, J = 7.4/1.2 Hz, 2 H, Har), 7.29-7.32 (m, 2 H, Har), 7.33 (d, J = 7.4 Hz, 2 H, Har), 7.37 (td, J = 7.4/1.2 Hz, 2 H, Har), 7.66 (d, J = 7.4 Hz, 2 H, Har); 13C NMR (CDCl3): delta = 4.43 (t, 1 C, ICH2), 55.20 (q, 1 C, CH3), 63.93 (t, 1 C, CH2O), 88.42 (s, 1 C, CH2OC), 113.55 (d, 2 C, Car), 120.00 (d, 2 C, Car), 125.43 (d, 2 C, Car), 126.84 (d, 2 C, Car), 128.23 (d, 2 C, Car), 129.15 (d, 2 C, Car), 135.29 (s, 1 C, Car), 140.51 (s, 2 C, Car), 146.87 (s, 2 C, Car), 158.83 (s, 1 C, Car); MS (EI, 70 eV) m/z (%): 442 (30, M+), 271 (100); HRMS (EI, 70 eV): (C22H19IO2) calc. 442.0430, found 442.0475; Anal. C22H19IO2 (C, H, I, O).

The synthetic route of 624-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kerscher-Hack, Silke; Renukappa-Gutke, Thejavathi; Hoefner, Georg; Wanner, Klaus T.; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 852 – 880;,
Iodide – Wikipedia,
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Electric Literature of 624-76-0,Some common heterocyclic compound, 624-76-0, name is 2-Iodoethanol, molecular formula is C2H5IO, 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.

Take a 50mL bottle,Add 2 mL of 2,3,3-trimethylhydrazine (6.22 mmol),1.46 mL 2-iodoethanol (9.33 mmol),And adding 20mL of CHCl3 as a solvent, under nitrogen protection,The reaction was carried out at 70 C for 48 h, cooled to room temperature and concentrated.A purple oil was obtained which was recrystallized twice from petroleum ether to give a purple solid.The yield was 70%.

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

Reference:
Patent; Jiangxi Science and Technology Normal University; Gao Fei; Shen Liang; Xu Dongdong; Zhong Jiang; Cao Zhiyuan; (8 pag.)CN108864155; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 391211-97-5, name is 3,4-Difluoro-2-((2-fluoro-4-iodophenyl)amino)benzoic acid, 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 391211-97-5, COA of Formula: C13H7F3INO2

A solution of 3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]benzoic acid (201 mg, 0.512 mmol), prepared using procedures similar to those described in US 7,019,033, 3-(2- aminopyrimidin-4-yl)azetidin-3-ol (87 mg, 0.52 mmol), benzotriazol-1-yl-oxy- tris(pyrrolidino)phosphonium hexafluorophosphate (293 mg, 0.563 mmol) and MN-diisopropylethylamine (270 uL, 2.82 mmol) in N,jV-dimethylformamide (2 mL) was stirred at room temperature for 2Oh. The mixture was partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer was separated and washed with brine, dried over sodium sulfate, filtered and the filtrate concentrated in vacuo. The residue was purified by reverse phase HPLC to afford the title compound 3-(2-aminopyrimidin-4-yl)-l-({3,4- difluoro-2-[(2-fluoro-4-iodophenyl)amino]phenyl}carbonyl)azetidin-3-ol (22 mg, 7%). 1H NMR (400 MHz, CD3OD): 8.23-8.20 (d, IH), 7.48-7.43 (d, IH), 7.35-7.32 (m, 2H), 7.09- 7.00 (m, IH), 6.88-6.84 (d, IH), 6.70-6.63 (t, IH), 4.59-4.54 (d, IH), 4.45-4.40 (d, IH), 4.23- 4.18 (d, IH), 3.04-3.99 (t, IH); MS (EI) for C20H15F3IN5O2: 542 (MH+).

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, 3,4-Difluoro-2-((2-fluoro-4-iodophenyl)amino)benzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EXELIXIS, INC.; WO2008/124085; (2008); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 20555-91-3, 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. 20555-91-3 name is 1,2-Dichloro-4-iodobenzene, 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.

Example HI; Preparation of l -(3,4-dichlorophenyl)-bicvclo[3 1 0]hexan-2-amines and 1-C3.4- dichlorophenyl)-bicvclo[3 1 0]hexan-3 -amines using Reaction Schemes 1 and 2A. Synthesis of 3-(3,4-diehlorophenyl)prop-2-vn-l-ol EPO Bis(t?phenylphosphine)palladium(II) chlonde (120 mg, 0 171 mmol) was added to a stirred solution of propargyl alcohol (5 24 g, 93 4 mmol, 1 02 eq), 1 -iodo- 3,4-dichlorobenzene (25 0 g, 91 6 mmol, 1 eq), t?ethylamine (18 5 g, 183 2 mmol, 2 eq), and copper iodide (60 mg, 0 32 mmol) in THF (50 mL) The mixture was stirred at 350C for 12 h under a nitrogen atmosphere The mixture was then filtered through a bed of celite and the filtrate was washed with ethyl acetate The filtrate was then concentrated at 350C (vac = 28 in Hg) using a rotary evaporator The residue was pu?fied using a silica gel column (4 1 heptane/ethyl acetate – ? 2 1 heptane/ethyl acetate) to give the desired product as a light yellow solid ( 17 10 g, 85 2 mmol, 93%) 1H NMR (400 MHz, CHLOROFORM-^) delta ppm 4 53 (s, 2H) 7 19 (d, I H) 7 29 (d, IH) 7 49 (s, IH)

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

Reference:
Patent; DOV PHARMACEUTICAL, INC.; WO2008/57575; (2008); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

111771-08-5, name is 2-Fluoro-6-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. COA of Formula: C7H4FIO2

EXAMPLE 2-162 4-Chloro-5-fluoro-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline Following the procedures described in Reference Example 2-5 and Example 2-1, the title compound was prepared from 2-fluoro-6-iodobenzoic acid and 1-(2-pyridinyl)-1H-pyrazol-5-ylamine (64% yield). mp: 173-176 C. (recrystallized from ethyl acetate). NMR (CDCl3) delta: 7.18-7.34 (2H, m), 7.66-7.79 (1H, m), 7.92-8.07 (2H, m), 8.62 (1H, s), 8.66-8.73 (2H, m).

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

Reference:
Patent; Uchikawa, Osamu; Mitsui, Keita; Asakawa, Akiko; Morimoto, Shigeru; Yamamoto, Masataka; Kimura, Hiroyuki; Moriya, Takeo; Mizuno, Masahiro; US2003/187014; (2003); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 627-32-7, 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. 627-32-7 name is 3-Iodo-1-propanol, 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.

General procedure: To a stirred solution of alcohol (1.0 equiv.) in CH2C12 (10 mL) at 0 C were added silyl chloride (1.1 equiv.) and imidazole (1.5 equiv.). The reaction mixture was allowed to room temperature, stirred until starting material was consumed. The reaction mixture was quenched by addition of saturated NaHCO3 (10 mL). The aqueous layer was extracted with CH2C12 (3 x 10 mL) and the organic extracts were washed with H20 (2 x 10 mL) and brine. The washed organic layers were dried over Na2504, filtered, concentrated, and purified by a silica gel column chromatography to yield pure product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Iodo-1-propanol, and friends who are interested can also refer to it.

Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; KISHI, Yoshito; YAHATA, Kenzo; KUMAR, Vemula, Praveen; VADDELA, Sudheer, Babu; (137 pag.)WO2019/9956; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 202982-68-1, name is 1-Chloro-4-fluoro-2-iodobenzene, molecular formula is C6H3ClFI, 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. Quality Control of 1-Chloro-4-fluoro-2-iodobenzene

To a suspension of 6-bromo- 1,2,3 ,4-tetrahydroisoquinolin- 1-one (1.0 g), 1-chloro-4-fluoro-2-iodobenzene (1.134 g), DMEDA (0.094 mL), and K3P04 (1.878 g) in toluene (10 mL) was added CuT (0.084 g) under nitrogen flow, and the mixture was stirred at 90C under nitrogen atmosphere overnight. Then, 1-chloro-4-fluoro-2-iodobenzene (0.3 g) was added thereto at room temperature, and the mixture was stirred at 90C under nitrogen atmosphere overnight. The mxiture was cooled, and then concentrated. The resulted crude product was purified by medium- pressure column chromatography (Hexane/AcOEt) to give 6-bromo-2-(2-chloro-S-fluorophenyl)- 1,2,3 ,4-tetrahydroisoquinolin- 1-one (0.75 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 202982-68-1, its application will become more common.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; KAN, Keizo; TAKUWA, Masatoshi; TANAKA, Hirotaka; FUJIWARA, Hideto; YAMABE, Hokuto; MATSUDA, Satoshi; OHDACHI, Kazuhiro; HANARI, Taiki; MENJO, Yasuhiro; URUSHIMA, Tatsuya; FUJITA, Shigekazu; (183 pag.)WO2019/4421; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 98-61-3, 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. 98-61-3, name is 4-Iodobenzenesulfonyl chloride belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a 100mL Schlenk tube, add 2.000g (30.5mmol) zinc powder, 3.0 ml dimethyldichlorosilane and 40 ml of 1,2-dichloroethane. Under the protection of nitrogen, use constant pressure dropping funnel to add dropwise 1.512g (5.0mmol) p-iodobenzenesulfonyl chloride, 1.5 ml of N,N-dimethylacetamide and 40 ml of 1,2-dichloroethane mixuture solution. Heat to 75 deg.C and react until zinc powder disappears. Then reduce the temperature to room temperature. Then add 10.0 ml of pyridine. Under stirring, add 5.0 ml (35.0mmol) acetyl chloride. Continue stirring at room temperature under nitrogen protection for 18h. After the reaction, filtration, washing, removing the solid, the filtrate drying, mixed with petroleum ether and ethyl acetate filtrate (150 : 1v/v) as developing solvent, chromatography column for separation, the spin vaporization of solvent, dried under vacuum to get the 1.3502g white solid, i.e., acetic acid-4-iodo thiophenol ester. Yield 97.1%.

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

Reference:
Patent; Liaoning University; Xia, Lixin; Li, Haihua; Wang, Jing; Zhang, Qian; Song, Peng; (10 pag.)CN105669507; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com