Tag: M.W=300-400

Electric Literature of 845866-78-6, A common heterocyclic compound, 845866-78-6, name is 1-Bromo-3-iodo-5-(trifluoromethoxy)benzene, molecular formula is C7H3BrF3IO, 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: 8-Mercaptoadenine (3.6 mmol), neocuproine hydrate (0.36 mmol), Cul (0.36 mmol), NaO-?-Bu (7.2 mmol), respective aryl iodide (10.8 mmol), and anhydrous DMF (24 mL) were taken in a round bottom flask flushed with nitrogen. The flask was sealed with Teflon tape, heated at 1 10 C, and magnetically stirred for 24-36 h under nitrogen. Solvent was removed under reduced pressure and the resulting residue was chromatographed (CH2Cl2:MeOH:AcOH, 20: 1 :0.5). [0223] 8-((3-Bromo-5-(trifluoromethoxy)phenyl)thio)-9H-purin-6-amine (2h). Obtained by method A as a light yellow solid in 41 % yield. MS (ESI): m/z 407.8 [M + H]+.

The synthetic route of 845866-78-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEMORIAL SLOAN-KETTERING CANCER CENTER; CHIOSIS, Gabriela; YAN, Pengrong; PATEL, Pallav; PATEL, Hardik J.; TALDONE, Tony; YANG, Chenghua; SUN, Weilin; OCHIANA, Stefan; WO2015/23976; (2015); A2;,
Iodide – Wikipedia,
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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. 1189352-83-7, name is 3-Chloro-5-iodobenzotrifluoride, A new synthetic method of this compound is introduced below., Formula: C7H3ClF3I

2)9- (4-methoxyphenyl) -10 anthracene boronate 3mmol,1-chloro-3-iodo-5-trifluoromethyl-4,6-dihydrosubstituted benzene 3 mmol,Tetrakis(triphenylphosphine)palladium 0.3 mmol,Toluene 120mL,30 mL of ethanol and 120 mmol of K2CO3 (formed as a solution with 30 mL of distilled water) were added to the reaction flask.Then vacuum the system,Nitrogen protection,The reaction was carried out at 110 C for 24 hours.After the reaction,extraction,Rotary evaporation,Column chromatography (eluent: n-hexane / dichloromethane = 1:1),Recrystallization gave the product A9.The yield was 69%. 3)Will A9 2mmol,Boronic acid pinacol ester 6mmol,Palladium acetate 0.2 mmol,2-dicyclohexylphosphine-2′,6′-dimethoxybiphenyl 0.4 mmol,Potassium acetate 6mmol,Add 1,4-dioxane 90mL to the reaction flask,Then vacuum the system,Nitrogen protection,The reaction was carried out at 105 C for 18 hours.After the reaction,extraction,Rotary evaporation,Column chromatography (eluent: n-hexane / dichloromethane = 2:1),Recrystallization to give the product B9,The yield was 68%. 4)The final product i is obtained by Suzuki coupling reaction: B9 1mmol,The product obtained in step 2 is 9-bromo-10-(4-cyano)benzoquinone 0.84 mmol.Catalyst tetrakis(triphenyl)phosphine palladium 0.12 mmol,Toluene 60mL,20mL of ethanol,K2CO3 33.6mmol (formed into solution with 20mL distilled water),Add to the reaction bottle,Under the protection of nitrogen,It was refluxed at 110 C for 24 h.After the reaction, the methanol is hot washed,Filtering,Recrystallization of toluene,Sublimation gives the final product.The yield was 69%.

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; Shaanxi Normal University; Hu Jianyong; Zhang Jiali; Zhao Zhen; Duan Xuewei; (24 pag.)CN109503427; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 249647-25-4, 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. 249647-25-4, name is 3-Bromo-4-iodobenzoic acid, This compound has unique chemical properties. The synthetic route is as follows.

Method 13: Synthesis of 5-(5-{2-r5-(3-bromo-4-iodophenyl)-l,2,4-oxadiazol-3-yll-3- meth lbutan-2-yl}pyridin-2-yl)pyrimidin-2-amine (Example 69)A suspension of R19 (163.3 mg, 0.50 mmol) and Iota,Gamma-carbonyldiimidazole (81.0 mg, 0.50 mmol) in THF (2.0 mL) is heated at 50C for 30 min. 1-8.4 (100.0 mg, 0.33 mmol) is added and the solution is heated under reflux for 3 hours. The mixture is cooled to room temperature and AcOH (0.2 mL) is added. The reaction mixture is stirred at 80C overnight. After cooling to room temperature, the mixture is poured into water and extracted with EtOAc. The organic layers are combined, dried over anhydrous Na2S04 and filtered. The solvent is removed under reduced pressure. Purification via silica gel column chromatography affords Example 69 (67.0 mg).

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BARTOLOZZI, Alessandra; BOSANAC, Todd; CHEN, Zhidong; DE LOMBAERT, Stephane; HUBER, John, D.; LIU, Weimin; LO, Ho Yin; LOKE, Pui Leng; RIETHER, Doris; TYE, Heather; WU, Lifen; ZINDELL, Renee, M.; WO2012/40137; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 206559-43-5, name is 5-Bromo-2-iodo-m-xylene, molecular formula is C8H8BrI, 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: C8H8BrI

2.5 M n-Butyllithium, in tetrahydrofuran, (1.42 ml, 3.54 mmol, 1.1 equiv.) was added dropwise to a solution of bromobenzene (0.34 ml, 3.22 mmol, 1.0 equiv.) in dry tetrahydrofuran (18 ml), under nitrogen at -78 C. and the mixture stirred for 30 minutes. Zinc chloride (0.48 g, 3.54 mmol, 1.1 equiv.) was added and the mixture allowed to warm to room temperature while stirring for 2 hours. Palladium tetrakistriphenylphosphine (0.19 g, 0.16 mmol, 0.05 equiv.) and a solution of 5-bromo-2-iodo-1,3-dimethyl-benzene (1.00 g, 3.22 mmol, 1.0 equiv.) in tetrahydrofuran (2 ml) were added and the mixture stirred at room temperature for 16 hours. The tetrahydrofuran was evaporated under reduced pressure and the crude product purified by column chromatography (SiO2, heptane). The fractions were combined to afford 4-bromo-2,6-dimethylbiphenyl, 278 mg (33% yield) as a clear oil deltaH (400 MHz; d4-methanol) 7.28-7.39 (3H, m), 7.18 (2H, s), 7.03 (2H, d), 1.90 (6H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 206559-43-5, its application will become more common.

Reference:
Patent; Gubler, Marcel; Haap, Wolfgang; Hebeisen, Paul; Kitas, Eric A.; Kuhn, Bernd; Minder, Rudolf E.; Schott, Brigitte; Wessel, Hans P.; US2007/281979; (2007); 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. 1427311-76-9, name is (S)-1-(4-Iodo-5-methoxy-2-nitrophenyl)-2,2-dimethylpropan-1-ol, A new synthetic method of this compound is introduced below., COA of Formula: C12H16INO4

DMAP (463 mg, 3.80 mmol) and MsCl (177 mu?, 2.28 mmol) were added to a solution of compound 4 (400 mg, 0.76 mmol) in anhydrous CH2CI2 (5.0 mL) at 0C under a nitrogen atmosphere. The reaction was stirred at 0C for 10 mins and at room temperature for another 3 hours. The reaction was then diluted with CH2CI2 (20 mL). The solution was applied on a short silica gel plug (2 x 3 cm) and was eluted quickly with a hexane/ethyl acetate/triethylamine solvent system (80 mL, volume ratio: 80/20/0.5). The eluent was concentrated in vacuo, and the residue was mixed with (5)-l-(4-iodo-5-methoxy-2- nitrophenyl)-2,2-dimethyl-l-propanol (500 mg, 1.37 mmol). The mixture was heated at 115C for 45 min under a nitrogen atmosphere, cooled to room temperature and dissolved in THF (10 mL). w-Bu4NF (526 mg, 1.67 mmol) was added and the mixture was stirred at room temperature for 12 hours and then concentrated in vacuo. The residue was dissolved in CH2CI2 (50 mL) and washed with brine (50 mL), and the aqueous phase was extracted with CH2CI2 (20 mL) two times. The combined organic phase was dried over Na2S04, concentrated in vacuo, and the residue was purified by silica gel chromatography to yield 6- chloro-9-(P-D-2′-deoxyribofuranosyl)-7-[(5)-l-(4-iodo-5-methoxy-2-nitrophenyl)-2,2- dimethyl-propyloxy]-methyl-7-deazapurine 51 (135 mg, 29% for three steps). 1H NMR (400 MHz, CDCl3): delta 8.56 (s, 1 H, H-2), 8.21 (s, 1 H, Ph-H), 7.34 (s, 1 H, H-8), 7.02 (s, 1 H, Ph- H), 6.35 (dd, 1 H, J= 6.0 and 8.8 Hz, Eta-Gamma), 5.20 (s, 1 H, Ph-CH), 4.76 (dd, 2 H, J= 12.4 and 36.4 Hz, 7-CH2), 4.74 (m, 1 H, H-3′), 4.13 (m, 1 H, H-4′), 3.96 (m, 1 H, H-5’a), 3.92 (s, 3 H, OCH3), 3.80 (m, 1 H, H-5’b), 2.85 (m, 1 H, H-2’a), 2.30 (m, 1 H, H-2’b), 0.83 (s, 9 H, C(CH3)3).

The synthetic route of 1427311-76-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LASERGEN, INC.; STUPI, Brian, Philip; LI, Hong; WU, Weidong; HERSH, Megan, N.; HERTZOG, David; MORRIS, Sidney, E.; METZKER, Michael, L.; WO2013/40257; (2013); 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. 14192-12-2, name is 2,5-Diiodobenzoic acid, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2,5-Diiodobenzoic acid

To an oven-dried seal tube, was added 2,5-diiodobenzoic acid 6b (74.8 mg, 0.2 mmol), CuI (3.8 mg, 0.02 mmol) and K2CO3 (55.2 mg, 0.4 mmol). The reaction tube was evacuated and backfilled with argon. 2-Propanol (1.0 mL), ethylene glycol (22.3 muL) and thiol 5 (30 muL, 0.22 mmol) were added by syringes at room temperature. The tube was heated to 80 oC and stirred for 68 h. The reaction mixture was then allowed to reach room temperature. The reaction mixture was then filtered and concentrated in vacuo. The crude product was purified using CombiFlash automated chromatography system (methanol / methylene chloride, 0% to 10%) to afford the desired product 7b as white solid.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 14192-12-2.

Reference:
Article; Zheng, Pinguan; Lieberman, Brian P.; Ploessl, Karl; Lemoine, Laetitia; Miller, Sara; Kung, Hank F.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 3; (2013); p. 869 – 872;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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

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

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