Author: Jessica.F

Reference of 34270-90-1,Some common heterocyclic compound, 34270-90-1, name is 1-Iodo-2-(2-iodoethoxy)ethane, molecular formula is C4H8I2O, 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 35 In 3 ml of dimethylformamide was dissolved 140 mg of 7alpha-[(2,3,6-trideoxy-3-amino-alpha-L-lyxo-hexopyranosyl)oxy]-9alpha-amino-9beta-acetyl-7,8,9,10-tetrahydro-6,11-dihydroxy-5,12-naphthacenedione (dihydrochloride, m.p. 176-180 C.; [alpha]D25 +149 (c=0.11, water)]. Then, to the solution were added 2.0 g of bis(2-iodoethyl) ether and 72 mg of triethylamine and this was stirred at room temperature overnight. The reaction mixture was poured into a saturated aqueous sodium bicarbonate solution and extracted with chloroform. Thereafter, the chloroform layer was washed with water, dried over sodium sulfate and the solvent was removed by distillation under reduced pressure to obtain a residue. This residue was purified by a silica gel column chromatography (eluant: 10% methanol/chloroform containing 0.5% aqueous ammonia) and then converted to hydrochloride with hydrochloric acid/ether to obtain 98 mg of d-7alpha-[(2,3,6-trideoxy-3-morpholino-alpha-L-lyxo-hexopyranosyl)oxy]-9alpha-amino-9beta-acetyl-7,8,9,10-tetrahydro-6,11-dihydroxy-5,12-naphthacenedione di-hydrochloride [m.p. 178 -179 C.; [alpha]D20 +156 (c=0.10, methanol)].

The synthetic route of 34270-90-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Pharmaceuticals Company; US4673668; (1987); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 2142-70-3, 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 2142-70-3 as follows.

General procedure: A tube was loaded with CuCl (50 mg, 0.50 mmol) and CsF (228 mg,1.50 mmol) and sealed with a rubber septum. Anhydrous acetonitrile (1 mL) was added and the mixture was cooled to 0 C. Diethyl [(trimethylsilyl)difluoromethyl]phosphonate (neat, 325 mg, 1.25 mmol) was added and the mixture was heated at 40C for 1 h, cooled to 0 C and stirred at this temperature for 1 h. Pd(PPh3)Cl2 (18 mg,0.025 mmol) was added followed by a solution of the corresponding iodoarene 1 (0.50 mmol) in MeCN (1 mL). The suspension was stirred for 16 h at 40C. The reaction mixture was diluted with diethyl ether(15 mL), the organic layer was washed with water (15 mL), Na2CO3 (concentrated solution, 15 mL), dried over Na2SO4, and solvents were carefully removed under vacuum. Reverse-phase chromatography (H2O/MeCN or MeOH, gradient: 9:1 to 0:1, rate: 1% MeCN or MeOH per minute) gave the product 2.

According to the analysis of related databases, 2142-70-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ivanova, Maria V.; Besset, Tatiana; Pannecoucke, Xavier; Poisson, Thomas; Synthesis; vol. 50; 4; (2018); p. 778 – 784;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 40400-15-5, 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 40400-15-5 as follows.

General procedure: A flask was equipped with a magnetic stir bar and charged with 1Hpyrrole-2-carbaldehyde (2a; 19.0 mg, 0.2 mmol, 1.0 equiv), 2-bromophenylacetonitrile(1a; 39.2 mg, 0.2 mmol, 1.0 equiv), and K3PO4(63.6 mg, 0.3 mmol, 1.5 equiv). The flask was evacuated and filledwith N2, and then anhydrous DMSO (2.0 mL) was introduced via a syringe.The flask was heated in a 130 C oil bath for 24 h, at which timeTLC analysis [petroleum ether (bp 60-90 C)-EtOAc, 10:1] indicatedcomplete consumption of 2a and 1a. The reaction mixture was cooledto r.t. and added to a sat. solution of NaCl (20 mL) and extracted withEtOAc (3 × 10 mL). The combined organic layers were dried (Na2SO4)and filtered. The filtrate was concentrated, and the residue was purified by column chromatography on SiO2 [petroleum ether (bp 60-90C)-EtOAc, 10:1 to 30:1] to give 3af; Yield: 59.2 mg (93%); fluorescent yellow solid; mp 205.6-207.1 C.

According to the analysis of related databases, 40400-15-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jiang, Zeng-Qiang; Miao, Da-Zhuang; Tong, Yao; Pan, Qiang; Li, Xiao-Tong; Hu, Ren-He; Han, Shi-Qing; Synthesis; vol. 47; 13; (2015); p. 1913 – 1921;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 2974-94-9, name is 1-Iodo-4-phenoxybenzene, 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: C12H9IO

Example 9 1-(2-{[3-(4-Phenoxyphenyl)-2-propynyl]oxy}ethyl)-1H-imidazo[4,5-c]quinolin-4-amine Using the general method of Example 7, 1-[2-(2-propynyloxy)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine (0.50 g, 1.88 mmol) was reacted with 4-iodophenyl phenyl ether (0.78 g, 2.63 mmol). The crude product was purified by column chromatography eluding with 95/5 dichloromethane/methanol to provide a solid. The solid was slurried with aqueous sodium hydroxide to remove salts and then purified by column chromatography eluding with 9/1 ethyl acetate/methanol to provide a solid. This material was further purified by column chromatography eluding with 99/1 ethyl acetate/methanol to provide 24 mg of 1-(2-{[3-(4-phenoxyphenyl)-2-propynyl]oxy}ethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a solid, m.p. 146-148 C. Analysis. Calculated for C27H22N4O2.(H2O)4/5: %C, 72.24; %H, 5.30; %N, 12.48. Found: %C, 71.82; %H, 4.85; %N, 12.35. 1H NMR (300 MHz, DMSO-d6) delta 8.18 (s, 1H), 8.12 (d, J=7.4 Hz, 1H), 7.62 (d, J=7.7 Hz, 1H), 7.41-7.47 (m, 3H), 7.18-7.27 (m, 4H), 7.06 (dd, J=7.6, 1.0 Hz, 2H), 6.90 (dd, J=6.7 Hz, 2H), 6.71 (s, 2H), 4.85 (t, J=5.1 Hz, 2H), 4.37 (s, 2H), 4.02 (t, J5.0 Hz, 2H); IR (KBr) 3444, 3070, 2928, 1500, 1230, cm-1; HRMS (EI) Calculated for C27H22N4O2 (M+) 434.1743, found 434.1748.

The synthetic route of 1-Iodo-4-phenoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; 3M Innovative Properties Company; US6677348; (2004); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 111771-08-5, The chemical industry reduces the impact on the environment during synthesis 111771-08-5, name is 2-Fluoro-6-iodobenzoic acid, I believe this compound will play a more active role in future production and life.

Step A: 2-Fluoro-6-iodo-benzoic acid methyl ester. To a 200 mL round- bottomed flask were added 2-fluoro-6-iodo-benzoic acid (7.5 g, 28.2 mmol), LiOH*H2O (1 .42 g, 33.8 mmol), and THF (100 mL). The resulting mixture was warmed to 50 C and stirred for 2 h. Dimethyl sulfate (4.03 mL, 42.3 mmol) was then added and the mixture was warmed to 65 C. After 2 h, the mixture was cooled to room temperature and NH4CI(aq) (50 mL, 13 wt% solution) was added. The two resulting layers were thoroughly mixed and then separated. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to a light brown oil (7.79 g, 99% yield). 1H NMR (400 MHz, CDCIs): 7.68 – 7.60 (m, 1 H), 7.15 – 7.06 (m, 2H), 3.98 (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, 2-Fluoro-6-iodobenzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50202; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 13194-68-8, name is 4-Iodo-2-methylaniline, 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 13194-68-8, Formula: C7H8IN

Compound 4 (5.67 g, 21.5 mmol) and dibutylhydroxytoluene (10 mg, 45 mumol) were dissolved in a mixed solution of toluene (10 ml) and dimethyl acetamide (10 ml). Thionyl chloride (1.50 ml, 20.7 mmol) was added dropwise to the resulting solution under ice cooling, and the solution was stirred at room temperature for 4 hours. Furthermore, a dimethyl acetamide solution (10 ml) of 4-iodo-2-methylaniline (2.00 g, 8.58 mmol) was added dropwise to the resulting solution under ice cooling, and the solution was stirred at 80 C. for 2 hours. After cooling the solution to room temperature, 1 N hydrochloric acid was added to the solution, followed by extraction with ethyl acetate. The organic layer obtained by the extraction was washed once with aqueous sodium bicarbonate and once with saline, respectively, and sodium sulfate was added to the washed organic layer. The obtained organic layer was filtered to collect the filtrate, and then the solvent was distilled off from the filtrate under reduced pressure. The resulting residue was purified by flash column chromatography to obtain Compound 8 (3.17 g) as a white solid.

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

Reference:
Patent; FUJIFILM Corporation; FUKUSHIMA, Yuki; GOTO, Ryoji; US2019/177268; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 103962-05-6,Some common heterocyclic compound, 103962-05-6, name is 1-Iodo-4-(trifluoromethoxy)benzene, molecular formula is C7H4F3IO, 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.

To a 250 mL reaction flask was added 3-bromo-1H-1,2,4-triazole (5 g, 33.8 mmol), CuI (0.644 g, 3.38 mmol) and Cs2CO3 (11.01 g, 33.8 mmol). The flask was evacuated/backfilled with nitrogen gas, and then DMSO (33.8 ml) and 1-iodo-4-(trifluoromethoxy)benzene (4.87 g, 16.90 mmol) were added. The reaction mixture was heated to 100° C. for 20 hours (h). The reaction was cooled to room temperature, diluted with EtOAc and filtered through a plug of Celite®. The Celite® was further washed with EtOAc. Water was added to the combined organics, and the layers were separated. The aqueous phase was neutralized to pH 7, and further extracted with EtOAc. The combined organics were concentrated in vacuo. Purification via flash column chromatography using EtOAc/hexanes as eluent to yield the title compound (3.78 g, 73percent): mp 69-70° C.; 1H NMR (400 MHz, CDCl3) delta 8.44 (s, 1H), 7.70 (d, J=8.9 Hz, 2H), 7.38 (d, J=8.5 Hz, 2H); 19F NMR (376 MHz, CDCl3) delta ?58.04; EIMS m/z 307 ([M]+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Iodo-4-(trifluoromethoxy)benzene, its application will become more common.

Reference:
Patent; Dow AgroSciences LLC; GIAMPIETRO, Natalie C.; CROUSE, Gary D.; WHITEKER, Gregory T.; US2014/275560; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 847685-01-2, name is 4,5-Difluoro-2-iodoaniline, molecular formula is C6H4F2IN, 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. name: 4,5-Difluoro-2-iodoaniline

A dark violet solution of 2-iodo-4,5-difluoroaniline (1a) (148 mg, 0.582 mmol), gold complex [AuPPh3NN] 2 (308 mg, 0.5 mmol),[Pd(PPh3)4] (52 mg, 0.045 mmol) in 7 ml of acetonitrile were stirred in an argon atmosphere at 60-65 C for 1 h. The reaction mixture was evaporated. The product was isolated by column chromatography on SiO2, using a mixture of methylenechloride with ethylacetate (3:1) as the eluent. Yield: 71 mg (50%), dark purple crystals, Tmelt = 140-141 C. UV spectrum(CH2Cl2), lambdamax, nm (lgepsilon): 240 (4.00), 260 (3.79), 346 (4.07), 578 (2.88). IR spectrum (KBr), v , cm-1: 3357, 3168 (NH2), 2996(C-H), 1646, 1592, 1502, 1355, 1143, 873, 788. Found, %: 55.07, 5.63, N 14.64. Calculated, %: 54.93, 5.63, N14.78.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 847685-01-2, its application will become more common.

Reference:
Article; Tretyakov; Makhneva; Politanskaya; Bagryanskaya, I. Yu.; Stass; Journal of Structural Chemistry; vol. 59; 3; (2018); p. 689 – 696; Zh. Strukt. Kim.; vol. 59; 3; (2018); p. 712 – 719,8;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 101335-11-9, 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.

Step 2: (E)-4-(2-(2-Chloro-4-fluorophenyl)-l-(4-(thiazol-5-yl)phenyl)but-l-en-l- yl)benzaldehyde[00394] A mixture of (Z)-4-(2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l-(4-(thiazol-5- yl)phenyl)but-l-en-l-yl)benzaldehyde (99 mg, 0.22 mmol), 2-chloro-4-fluoro-l-iodobenzene (114 mg, 0.44 mmol), Pd(PPh3)2Cl2(15 mg, 0.022 mmol), and KOH (6M, 0.2 mL, 1.32 mmol) in 1,4-dioxane (2.2 mL) was heated to 90C overnight. After cooling, ethyl acetate and brine were added to the reaction mixture and the two layers were separated. The organic layer was washed with more brine, dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography on silica gel to afford 68 mg of a mixture of the title compound (major) and the undesired regioisomer (minor). 1H NMR (400 MHz, DMSO-d6) of major: delta 9.84 (s, 1H), 9.11 (s, 1H), 8.35 (s, 1H), 7.75 (d, 2H), 7.64 (d, 2H), 7.40-7.33 (m, 4H), 7.17 (m, 3H), 2.45 (q, 2H), 0.93 (t, 3H).

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-4-fluoro-1-iodobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SERAGON PHARMACEUTICALS, INC.; SMITH, Nicholas, D.; GOVEK, Steven, P.; KAHRAMAN, Mehmet; BONNEFOUS, Celine; JULIEN, Jackaline, D.; WO2014/151899; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 112671-42-8, name is 4-Bromo-1-iodo-2-nitrobenzene, 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 112671-42-8, name: 4-Bromo-1-iodo-2-nitrobenzene

Intermediate M1 – a (5.1 g, 18.4 mmol) with 2 – iodo -5 – bromo nitrobenzene (15.3 g, 46.7 mmol), sodium tertiary butyl alcohol (7.1 g, 74.4 mmol), toluene 100 ml, nitrogen protection, 0.3 gPd2(Dba)3, Tri-[…] (20 ml, 10% toluene solution), open mixing, heating to 100 C reflux, the reaction 12 h, washing the reaction solution, the organic phase is concentrated, over silica gel column, eluent ethyl acetate is petroleum ether=50 1, concentrated eluent, get midbody M1 – b (9.2 g, yield 73.9%).

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-Bromo-1-iodo-2-nitrobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Beijing Dingcai Technology Co., Ltd.; Gu’an Dingcai Technology Co., Ltd.; Fan Hongtao; Xing Qifeng; Zhang Wei; Zhang Xianghui; (25 pag.)CN107880051; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com