Tag: M.W=200-300

Synthetic Route of 181765-85-5, These common heterocyclic compound, 181765-85-5, name is Methyl 4-chloro-2-iodobenzoate, 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: To a solution of the corresponding benzoate (1.0 equiv) in dry THF (2.0 mL per 1.0 mmol of benzoate) under N2 atm was cooled to -40 C. Then, i-PrMgCl (2.0 equiv, 2M in THF) was added dropwise and stirred for 0.5 h at the same temperature. Afterwards CuCN.2LiCl (0.1 equiv) was added and after 5 minutes 2-chloro-3-iodo-propene (2.0 equiv) were added slowly. Then, the reaction was allowed to warm up at room temperature for 1.5 h. The reaction was quenched with saturated aqueous NH4Cl and extracted with diethyl ether. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, concentrated by rotary evaporation, and purified by column chromatography to give 22a and 22b.

The synthetic route of 181765-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jorgensen, William L.; Anderson, Karen S.; US2015/105351; (2015); A1;,
Iodide – Wikipedia,
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Some common heterocyclic compound, 52548-63-7, name is 5-Fluoro-2-iodobenzoic acid, molecular formula is C7H4FIO2, 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. SDS of cas: 52548-63-7

To a mixture of tert-butyl 4-(1H-pyrrolo[2,3-c]pyridin-3-yl)piperidine-1- carboxylate (10 g, 0.03 mol) in DMF (200 mL) was added 5-fluoro-2-iodobenzoic acid (8.3 g, 0.03 mol), Cu (384 mg, 0.01 mol) and K2CO3 (12 g, 0.09 mol). The mixture was degassed and purged with N23 times followed by heating under N2 at 130oC for 17 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was added to water (500 mL) and 3 M HCl (aq.) to a pH = 3-4, extracted with EtOAc/i-PrOH (v/v, 10/3, 3 ¡Á 400 mL), and the combined organic layers were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated under reduced pressure to give 2-(3-(1-(tert-butoxycarbonyl)piperidin-4-yl)-1H-pyrrolo[2,3- c]pyridin-1-yl)-5-fluorobenzoic acid as brown solid. Yield: 14 g (100% crude); LCMS method C: Rt= 0.645 min; (M+H)+= 440.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 52548-63-7, its application will become more common.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CACATIAN, Salvacion; CLAREMON, David A.; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen D.; SINGH, Suresh B.; VENKATRAMAN, Shankar; YUAN, Jing; ZHENG, Yajun; ZHUANG, Linghang; (285 pag.)WO2018/53267; (2018); A1;,
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Application of 18282-51-4, These common heterocyclic compound, 18282-51-4, name is (4-Iodophenyl)methanol, 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.

In a 10 mL round bottom flask, 1.17 g of 4-iodobenzyl alcohol and 2 g of diethylene glycol dimethyl ether were sequentially added.The resulting mixture was subjected to ultrasonic irradiation at 40 kHz/30 W/70 C for 30 minutes in an ultrasonic reaction apparatus. Diethylene glycol dimethyl ether was removed under reduced pressure and recrystallized to give 1.15 g of 4-iodobenzoic acid, yield 93%.

The synthetic route of 18282-51-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Central South University; Xiao Fang; Xiao Yuanyuan; Zeng Ming; Li Na; Yin Lirong; (15 pag.)CN108467342; (2018); A;,
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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. Application In Synthesis of 1-Iodo-4-(trifluoromethoxy)benzene

Step A: Preparation of 2-bromo-5-(4-(trifluoromethoxy)phenyl)pyridine. [00137] To a microwave vial equipped with a magnetic stir bar were added (6-bromopyridin-3- yl)boronic acid (1.37 g, 6.77 mmol), l-iodo-4-(trifluoromethoxy)benzene (1.5 g, 5.21 mmol) and DMF (11.9 mL), followed by K2C03 (2.52 g, 18.2 mmol) and water (2.98 mL). The reaction mixture was stirred under N2 for 5 min and treated with Pd(PPh )4 (16.05 mg, 0.014 mmol). The reaction vessel was capped, placed in a Biotage Initiator microwave reactor for 1 h at 120 ¡ãC, with external IR-sensor temperature monitoring from the side of the vessel. The cooled reaction mixture was filtered through a pad of Celite? rinsing with EtOAc (100 mL), and the filtrate was washed successively with saturated aqueous NaHC03 (50 mL), water (3 x 50 mL), and brine (50 mL). The organic phase was dried over MgS04, filtered, and concentrated. The residue was purified by column chromatography (Si02, 0-M0 EtOAc in hexanes) to give the title compound (1.07 g, 63percent) as an off-white solid: IR (Thin Film) 3036, 1453, 1210, 1167 cm”1; 1H NMR (400 MHz, CDC13) delta 8.57 (dd, J = 2.6, 0.8 Hz, 1H), 7.71 (dd, J= 8.2, 2.6 Hz, 1H), 7.63 – 7.54 (m, 3H), 7.38 – 7.29 (m, 2H); 19F NMR (376 MHz, CDC13) delta -57.83; HRMS-ESI (m/z) [M+H]+ calcd for Ci2H8BrF3NO, 317.9736; found, 317.9735.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 103962-05-6, its application will become more common.

Reference:
Patent; DOW AGROSCIENCES LLC; LOSO, Michael R.; GUSTAFSON, Gary D.; KUBOTA, Asako; YAP, Maurice C.; BUCHAN, Zachary A.; STEWARD, Kimberly M.; SULLENBERGER, Michael T.; HOEKSTRA, William J.; YATES, Christopher M.; WO2015/160665; (2015); A1;,
Iodide – Wikipedia,
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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. 103440-55-7, name is Methyl 2-iodo-6-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 103440-55-7

Methyl 2-iodo~6-methybenzoate (158) (2.00 g, 7.245 mmoi) and NBS (1.418 g, 7.969 mmol) were stirred in chiorobenzene (50 mL) and benzoyl peroxide (75% w/w, 0.234 g, 0.724 mmol) was added. The reaction was stirred at 90 C for 18 hours, cooled to room temperature, filtered and the precipitate was washed with cyclohexane (4×10 mL). The combined filtrates were evaporated, and the resulting brown oil was diluted with THF (50 mL). Aqueous ammonia solution (20 mL) was added, and the mixture was stirred vigorously for 17 hours. The mixture was diluted with water (20 mL) and the THF was removed in vacuo. DCM (150 mL) was added, the layers were separated and the aqueous layer was extracted with DCM (2×100 mL), the combined organics were washed with brine (100 mL), dried (MgS04) and filtered. Silica gel was added and the voiatiles were removed in vacuo to give the crude material absorbed onto silica gel. The material was purified by silica gel chromatography (Biotage Isolera, 40 g Si cartridge, 0- 00% EtOAc in petroleum benzine 40-60 C, then 0-20% methanol in EtOAc) to give the title compound (159) (0.757 g, 40% yield) as a beige solid; 1H NMR (400 MHz, CDCI3) delta 7.93 (dd, J = 7.8, 0.7 Hz, 1 H), 7.46 (dd, J = 7.5, 0.8 Hz, 1 H), 7.26 – 7.21 (m, 1 H), 7.10 (br s, 1 H), 4.37 (d, J = 0.6 Hz, 2H). LCMS Method C: rt 5,06 min; m/z 260.0 [M+Hf .

According to the analysis of related databases, 103440-55-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LTD; DEVLIN, Mark Graeme; STREET, Ian Philip; TONG, Warwick Bonner; WO2014/27199; (2014); A1;,
Iodide – Wikipedia,
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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 156150-67-3 as follows. Quality Control of 2-Chloro-1-fluoro-4-iodobenzene

To the stannane (0.39 g, 0.95 mmol) in DMF (10 ml) was added the 2-chloro-4-fluoroiodobenzene (0.73 g, 2.86 mmol), Cul (0.19 g, 1.05 mmol) and tetrakis(triphenylphosphine)palladium (0) (0.11 g, 0.095 mmol). The reaction was stirred at RT under N2 for 21 h. The reaction mixture was added to Et2O and the heterogeneous solution filtered through a bed of celite, washing with EtOAc. The filtrate was washed with water and brine and dried (MgSO4). Filtration and evaporation of the solvent in vacuo afforded a residue that was preadsorbed on silica gel. Purification by silica gel chromatography (4% EtOAc/hexane) yielded the arylacrylate (0.19 g, 78%), which was used directly in the next step.

According to the analysis of related databases, 156150-67-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Schering Corporation; US6391865; (2002); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 138385-59-8, 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. 138385-59-8, name is 4-Iodo-2,6-dimethylaniline hydrochloride belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(Z)-Methyl 3-(4-amino-3,5-dimethylphenyl)-2-(benzyloxycarbonyl)acrylate.; A 2 L round bottom flask was charged 4-iodo-2,6-dimethylbenzenaminehydrochloride salt (55 g, 194 mmoles), methyl 2-(benzyloxycarbonyl)acrylate (59.2 g, 252 mmoles), tetrabutylammonium chloride (59.2 g, 213 mmoles), palladium (II) acetate (4.34 g, 19.4 mmoles), and tetrahydrofuran (1.2 L, degassed by a flow of nitrogen for 30 min). The mixture was stirred so that a suspension was formed and then degassed by a flow of nitrogen for 30 min. Triethylamine (1 10 mL, 789 mmoles) was added and the resulting mixture was heated at reflux for 3 h. After cooling to room temperature, the reaction mixture was filtered through a pad of celite, washed with tetrahydrofuran (2 x 100 mL), and concentrated. The residue was dissolved in dichloromethane, washed with water (3X) and brine (2X), dried over sodium sulfate, and concentrated. Flash chromatography (silica gel, using 1 :9 ethyl acetate/dichloromethane) gave a tan solid. The solid was recrystallized from warm methanol (210 mL) and water (100 mL). The mixture was held at room temperature overnight, then at 0C for 2 h, and finally at -15C for 2 h. The resulting solid was filtered, washed with ice cold 1 : 1 methanol/water, and dried under high vacuum overnight to give 44.7 g (65%) as a light tan solid which was a mixture of Z/E isomers (73:27). XH-NMR (DMSO-d6) delta, 2.05 (s, 6 H), 3.61 (s, 0.8 H), 3.68 (s, 2.2 H), 5.00 (s, 0.54 H), 5.13 (s, 1.46 H), 5.24 (s, 2 H), 7.40-7.21 (m, 8 H), 8.51 (s, 0.27 H), 8.79 (s, 0.73 H); 1 jC-NMR (DMSO-d6) delta 17.8, 51.7, 65.3, 1 19.4, 120.0, 120.3, 127.3, 127.7, 128.3, 130.9, 135.8, 137.2, 146.9, 154.7, 166.0.

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-2,6-dimethylaniline hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CHATURVEDULA, Prasad V.; DUBOWCHIK, Gene M.; MACOR, John E.; WO2011/123232; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 101066-87-9, name is 4-Iodo-2-(trifluoromethyl)benzonitrile, 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. Safety of 4-Iodo-2-(trifluoromethyl)benzonitrile

[0443] A suspension of trans-1-(4-methoxybenzyl)hexahydropyrano[3,4-d]imidazol-2(3H)-one [racemic (¡À)] (0.25 g, 0.95 mmol), 4-iodo-2-(trifluoromethyl)benzonitrile (0.28 g, 0.95 mmol), trans-N,N?-dimethylcyclohexane-1,2-diamine (0.032 g, 0.29 mmol) and potassium carbonate (0.395 g, 2.86 mmol) in toluene (15 mL) was degassed for 30 min in a microwave vial. CuI (0.009 g, 0.05 mmol) was added and the vial was sealed with an aluminum cap. The sealed vial was kept in a preheated oil bath at 110 C. and stirred for 12 h. The reaction mixture was cooled to RT, filtered through a pad of celite, and filtrates were concentrated under reduced pressure to give a black residue. The residue was purified by column chromatography on silica gel (dichloromethane/methanol=100:0 to 99:1) to give the title compound (0.17 g, 41.0%) as an off white solid. LCMS: m/z 432.1 [M+H]+; 1H NMR (400 MHz, CDCl3) delta 7.80-7.74 (m, 2H), 7.54 (d, 1H), 7.20 (d, 2H), 6.84 (d, 2H), 4.50 (d, 1H), 4.40-4.30 (m, 2H), 4.15-4.05 (m, 1H), 3.80 (s, 3H), 3.65 (ddd, 1H), 3.50-3.20 (m, 2H), 3.10 (ddd, 1H), 1.90 (d, 1H), 1.72-1.68 (m, 1H).

The synthetic route of 4-Iodo-2-(trifluoromethyl)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bock, Mark Gary; Chikkanna, Dinesh; Gerspacher, Marc; Khairnar, Vinayak; Lagu, Bharat; Pandit, Chetan; US2014/329858; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 13421-00-6, name is 5-Chloro-2-iodobenzoic acid belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 5-Chloro-2-iodobenzoic acid

General procedure: A dry sealable vial was charged with sulfonimidamide 4a (368 mg, 2.00 mmol), 2-iodobenzoic acid (494 mg, 2.00 mmol), CuI (76 mg, 0.40 mmol), and K2CO3 (690 mg, 5.00 mmol) in anhyd DMF (5.0 mL). After heating to 100 C for 2 h, the heterogeneous mixture was cooled to r.t. The mixture was diluted with water (10 mL), acidified with 2 M HCl and extracted with EtOAc (3 ¡Á 30 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by CombiFlash chromatography (silica gel, n-hexane/EtOAc, 6:4) to afford the desired product 7a as a cream solid; yield: 633 mg (90%).

The synthetic route of 13421-00-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sen, Indira; Sasmal, Swarnendu; Hall, Roger G.; Pal, Sitaram; Synthesis; vol. 48; 21; (2016); p. 3743 – 3752;,
Iodide – Wikipedia,
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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. 69113-59-3, name is 3-Iodobenzonitrile belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 3-Iodobenzonitrile

General procedure: Aryl-halide (0.2 mmol, 1 equiv.), Ir(dtbbpy)(ppy)2PF6 (1.8 mg, 0.002 mmol, 1 mol %), NiCl2.glyme (4.4mg, 0.02 mmol, 10 mol %), DMSO (2.0 mL) was added to a 10 mL schlenk flask equipped with a magnetic stirrer bar. This resulting mixture was sealed and degassed via vacuum evacuation and subsequent backfill with ethylene for three times. Then, N,N,N?,N?-tetramethylethylenediamine, TMEDA(60 muL, 2 equiv.), N,N-diisopropylethylamine, DIPEA (70 muL, 2 equiv.) and H2O (7.2 muL, 2 equiv.) were subsequently added in this order. The mixture was then irradiated with blue LED (2 meter strip, 18 W)with ethylene balloon for 24 hours at 80oC (Figure S1). The reaction was added water (30 mL) and extracted with ethyl acetate (10 mL) three times. Combined organic layer was successively washed with brine three times and dried over Na2SO4 and concentrated under reduced pressure. The residue was then subjected to flash column chromatography (hexane or hexane/ethyl acetate) to yield theproduct

The synthetic route of 69113-59-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Jiesheng; Luo, Yixin; Cheo, Han Wen; Lan, Yu; Wu, Jie; Chem; vol. 5; 1; (2019); p. 192 – 203;,
Iodide – Wikipedia,
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