Tag: M.W=200-300

Some common heterocyclic compound, 16932-44-8, name is 2-Iodo-1,3-dimethoxybenzene, molecular formula is C8H9IO2, 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. COA of Formula: C8H9IO2

General procedure: An argon-filled flask wasadd the respective aryl halide (1.0 mmol), CuI (20 mg, 0.1 mmol, 10 mol%), L3(37 mg, 0.1 mmol, 10 mol%), KOH (168 mg, 3 mmol), thiol (1.5 mmol) and glycerol(10 mL). The contents were then stirred at 100 C for 24 h. After that, themixture was cool to room temperature, diluted with ethyl acetate (20 mL) and washedwith saturated NaCl solution (3 x 20 mL). The organic layer was separated,dried over MgSO4 and concentrated under vacuum. The crude productwas purified by flash chromatography on silica gel using hexane /ethyl acetateas eluent

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16932-44-8, its application will become more common.

Reference:
Article; Cargnelutti, Roberta; Lang, Ernesto S.; Schumacher, Ricardo F.; Tetrahedron Letters; vol. 56; 37; (2015); p. 5218 – 5222;,
Iodide – Wikipedia,
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Related Products of 25309-64-2, These common heterocyclic compound, 25309-64-2, name is 1-Ethyl-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.

General procedure: To astirred solution of: Aryl iodide (1.0 mmol), trans-4-Hydroxy-L-proline (1.5 mmol), nano CuFe2O4 (0.01 mmol), base (2 equiv), solvent (3.0 mL), 20h, 100 oC. The progress of the reaction was monitored by TLC. After the reaction was complete CuFe2O4 nano were placed on the bottom of the flask by a neodymium magnet, and the supernatant solution was removed. The crude residue was extracted with ethyl acetate (3 x 10 mL). The combined organic layers were extracted with water, saturated brine solution, and dried over anhydrous Na2SO4.The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography to give the corresponding N-substituted pyrrole in excellent yields. The identity and purity of the product were confirmed by 1H,13C NMR, and mass spectra.

The synthetic route of 25309-64-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Satish; Reddy, K. Harsha Vardhan; Ramesh; Kumar, B.S.P. Anil; Nageswar; Tetrahedron Letters; vol. 55; 16; (2014); p. 2596 – 2599;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 13421-13-1, 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. 13421-13-1 name is 4-Chloro-2-iodobenzoic acid, 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.

1) Synthesis of 4-chloro-2-(4-methoxyphenylthio)benzoic acid (Reference Example compound 2-1) [0185] 4-chloro-2-iodobenzoic acid (20.0 g), 4-methoxybenzenethiol (8.71 ml), potassium hydroxide (15.4 g), copper powder (0.48 g) and water (240 ml) was stirred under reflux for 4 hr. The reaction mixture was poured into a mixed solution of ethyl acetate and 1M hydrochloric acid, and the organic layer was separated. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was washed in diisopropyl ether and hexane (1:8) to give Reference Example compound 2-1 (18.8 g) as a white powder. 1H-NMR (CDCl3) delta (ppm) : 3.89 (3H, s), 6.69 (1H, d, J = 1.8 Hz), 7.01 (2H, d, J = 8.6 Hz), 7.09 (1H, dd, J = 2.0, 8.3 Hz, 7.50 (2H, d, J = 8.6 Hz), 8.04 (1H, d, J = 8.5 Hz).

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

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; HAMADA, Maiko; TASHIRO, Kaoru; SAKASHITA, Hiroshi; KIUCHI, Masatoshi; TAKEDA, Shuzo; ADACHI, Kunitomo; EP2842937; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 619-58-9,Some common heterocyclic compound, 619-58-9, name is 4-Iodobenzoic acid, molecular formula is C7H5IO2, 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 100-mL resealable reaction tube, 4-iodobenzoic acid (10.0 g, 40.03 mmol) and furan-2- ylboronic acid (8.95 g, 80.06 mmol) were dissolved in degassed DMF (250 mL) and water (50 mL) at rt under nitrogen atmosphere. Pd(PPli3)4 (4.65 g, 3.99 mmol), K2CO3 (16.6 g, 120.09 mmol) were sequentially added to the above solution under nitrogen atmosphere. The resulting mixture was degassed by purging argon gas for 15 min, and reaction mixture was heated to 90C until completion of the reaction (TLC). The reaction mixture was cooled to rt, diluted with cold water and washed with ethyl acetate (3 x 30 mLl.The aqueous layer was separated and acidified to pH 3 with concentrated HC1, before extracting with EtOAc (100 mL x 2). The combined extract was washed with brine and concentrated under reduced pressure to get title compound (6.92 g, 92%) as light yellow solid. LCMS (m/: 187 (M-l)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Iodobenzoic acid, its application will become more common.

Reference:
Patent; SALK INSTITUTE FOR BIOLOGICAL STUDIES; MITOKYNE, INC.; EVANS, Ronald; BAIGA, Thomas, J.; BOCK, Mark, G.; DOWNES, Michael; EMBLER, Emi, Kanakubo; FAN, Weiwei; KEANA, John, F.W.; KLUGE, Arthur, F.; NOEL, Joseph, P.; PATANE, Mike, A.; WO2014/165827; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

116632-39-4, name is 5-Bromo-2-iodotoluene, 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. Recommanded Product: 116632-39-4

A mixture of 5-bromo-2-iodotoluene (25.0g, 0.1mol), NBS (36.6g, 0.1mol), and BPO (0.6g, 2.6mmol) were dissolved in 200mL of CCl4 and refluxed. The mixture was allowed to stir until the completion of the reaction, which was confirmed by thin layer chromatography (TLC) analysis (7h). When the reaction ended, a large amount of the floating succinimide produced in the reaction systems was filtrated off. The filtrate was evaporated to remove the solvent. The crude product was purified by column chromatography on silica with petroleum ether as the eluent to give 16.3g of a white solid 5-bromo-2-iodobenzyl bromide. Yield:50%; 1H NMR (600MHz, CDCl3): delta=4.52 (s, 2H, Ph-CH2), 7.21-7.59(m, 3H, Ar-H) ppm.

The synthetic route of 116632-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guan; Jia; Zhang; Zhang; Ma; Lu; Lai; Lei; Dyes and Pigments; vol. 136; (2017); p. 873 – 880;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 5460-32-2, These common heterocyclic compound, 5460-32-2, name is 4-Iodo-1,2-dimethoxybenzene, 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.

A mixture of I (117.0 g, 590 mmol), 4-iodo-1,2-dimethoxybenzene (85.0 g, 590 mmol), Pd(OAc)2 (13.2 g, 59 mmol) and tri(o-tolyl)phosphine (36.0 g, 118 mmol) in triethylamine (3 L) was heated at 90° C. for 12 h. The mixture was cooled to room temperature and diluted with ethyl acetate (3 L). The organic phase was washed with brine, dried (MgSO4), and concentrated in vacuo to dryness. The crude product was purified by silica gel chromatography (0 to 40percent ethyl acetate/hexanes) to provide (la) as a brown oil (87.0 g, 73percent based on the recovered starting material). 1H NMR (300 MHz, CDCl3): delta 6.85 (s, 2H), 6.79 (s, 1H), 6.64 (s, 1H), 3.98-3.93 (m, 4H), 3.88 (s, 3H), 3.86 (s, 3H), 2.10-2.00 (m, 4H), 1.81 (s, 3H), 1.68 (d, J=12.9 Hz, 4H), 1.17 (s, 1H)

Statistics shows that 4-Iodo-1,2-dimethoxybenzene is playing an increasingly important role. we look forward to future research findings about 5460-32-2.

Reference:
Patent; Sequoia Sciences, Inc.; Williams, Russell B; Eldridge, Gary; Starks, Courtney M.; Guzzo, Peter Robert; Huang, Zhongping; (100 pag.)US9562031; (2017); B1;,
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. 58755-70-7, name is 1-Iodo-4-methoxy-2-nitrobenzene, A new synthetic method of this compound is introduced below., COA of Formula: C7H6INO3

Compound 4 To a solution containing compound 3 (240 mg, 1.25 mmol) and 4-iodo-3-nitroanisole (345 mg, 1.24 mmol) were added PdCI2(PPh3)2 (44 mg, 5.0 mol %), and CuI (12 mg, 5.0 mol %) in TEA (15 mL). The mixture was stirred at 550C for 3 h, cooled, and filtered. The filtrate was concentrated under reduced pressure. Chromatography of the residue on silica gel (Hex:AcOEt = 100:40 (v/v)) gave 380 mg (88%) of compound 4.

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; THRESHOLD PHARMACEUTICALS, INC.; WO2006/57946; (2006); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 105202-02-6, 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. 105202-02-6, name is 2-Iodo-5-(trifluoromethyl)aniline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: PdCl2(PPh3)2 (35.1 mg, 0.05 mmol), CuI (9.5 mg, 0.05 mmol), PPh3 (13.1 mg, 0.05 mmol) and iodoaniline derivatives (1.00 mmol) were stirred under N2 in a mixed solvent with CH3CN (5 mL) and Et3N (1 mL). The alkyne (1.20 mmol) was added to the mixture and stirred in reflux. The reaction was monitored by TLC. After completion, H2O (10 mL) was added to the reaction mixture and extracted with ethyl acetate (3 × 10 mL). The combined organic solution was washed with brine, dried over anhydrous MgSO4, concentrated at the reduced pressure. And the crude product was purified by column chromatography to give 2-alkynylanilines.

The chemical industry reduces the impact on the environment during synthesis 2-Iodo-5-(trifluoromethyl)aniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Sheng-Yan; Sun, Shan-Gang; Guo, Yu-Shuang; Lu, Xiao-Fan; Guo, Dian-Shun; Tetrahedron Letters; vol. 59; 41; (2018); p. 3719 – 3723;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 52807-27-9,Some common heterocyclic compound, 52807-27-9, name is 4-Chloro-2-iodoanisole, molecular formula is C7H6ClIO, 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.

4-Chloro-2-iodophenol; 109.4g (0.436mol) of boron tribromide were added over 10 minutes to a stirred solution of 9Og (0.335mol) of 4-chloro-2-iodoanisole in dichloromethane (900ml) at -780C under nitrogen. Cooling was removed and allowed to warm to room temperature and stirred for 5 hours. Poured onto ice and diluted with a further 800ml of water. The organic phase was separated, the aqueous extracted with dichloromethane and the combined organics washed with saturated sodium bicarbonate, dried and evaporated to give 84.87g of off- white solid; Sodium 6-r(5-chloro-2-fr(4-chloro-2-fluorophenyl)methvnoxy)phenyl)methvn-2- pyridinecarboxylate (Alternative route 2); 4-Chloro-2-iodophenol; Boron tribromide (1349g) was added to a solution of 4-chloro-2-iodoanisole (1025g) in dichloromethane (10.3L) under nitrogen at such a rate that the temperature remained at 0- 5C The solution was then warmed to 200C and stirred for c. 19h until the reaction was complete by HPLC. This organic solution was added to water (8.2L) and the mixture was cooled to 5C to 10C. DCM (770ml) was added and the resuting biphasic mixture was then stirred at 50C for 15 min before being warmed to 220C and then finally stirred at 22C for 20 min before separating the phases. The separated organic phase was washed with aqueous saturated sodium bicarbonate (3.1L), water (3.1L) and then evaporated on a Buchi to give the title compound. (963.6g)

The synthetic route of 52807-27-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/66968; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 6213-88-3,Some common heterocyclic compound, 6213-88-3, name is (E)-Methyl 3-iodoacrylate, molecular formula is C4H5IO2, 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.

Method 1: To a dry Schlenk flask was added Pd(OAc)2 (36 mg,0.16 mmol), P(o-tol)3 (0.10 g, 0.33 mmol) and AgOAc (0.601 g,3.60 mmol). The flask was purged with argon, and dry, degassed MeCN (10 mL) was added. 4,4,6-Trimethyl-2-vinyl-1,3,2-dioxaborinane (0.655 mL, 3.80 mmol) was then added, followed by methyl (2E)-3-iodoprop-2-enoate (0.704 g, 3.32 mmol). The vessel was purged further with argon, and the reaction mixture was then heated to 50 C with vigorous stirring for 2 days. The mixture was allowed to cool, then diluted with Et2O (280 mL) and passed through a short Celite/silica plug. The organic extracts were washed with 5% HCl (40 mL), H2O (80 mL) and brine (80 mL), dried over MgSO4, filtered and evaporated to yield 0.98 g of crude product as an orange oil. The crude product was purified by silica gel chromatography, eluent 10% EtOAc in hexane elution. Pure fractions were evaporated to yield (2E,4E)-5-(4,4,6-trimethyl-[1,3,2-dioxaborinan-2-yl]-penta-2,4-dienoic acid methyl ester as a yellow oil (0.404 g, 51%). 1H NMR (400 MHz, CDCl3): delta 1.35-1.24 (9H, m), 1.5-1.47 (1H, m), 1.81 (1H, dd, J = 14.0, 2.9 Hz), 3.75 (3H, s), 4.24 (1H, dqd, J = 12.3, 6.2, 2.9 Hz), 5.99-5.86 (2H, m), 6.97 (1H, ddd, J = 17.3, 11.0, 0.7 Hz), 7.33-7.21 (1H, m); 11B NMR (128 MHz, CDCl3): delta 25.52; 13C NMR (101 MHz, CDCl3): delta 23.58, 28.62, 31.65, 46.41,52.12, 65.52, 71.67, 123.17, 143.89, 146.54, 167.93; IR (upsilonmax, cm-1) 2974.3 (w) 1719.5 (s) inter alia; LCMS (ESI) 239.2; HRMS (ESI) calculated [C12H19BO4H] 238.1470, found 238.1491. Method 2: To a dry flask was added methyl (2E)-3-iodoprop-2-enoate (2.82 g, 13.3 mmol), Pd(OAc)2 (0.150 g, 0.67 mmol), P(otol)3 (0.408 g, 1.34 mmol) and AgOAc (2.41 g, 14.4 mmol). The flask was purged with argon, and dry, degassed MeCN (80 mL) wasadded. 4,4,6-Trimethyl-2-vinyl-1,3,2-dioxaborinane (2.6 mL,15 mmol) was then added, the vessel was purged further with argon, and the reaction mixture was then heated to 50 C with vigorous stirring for 23h. The mixture was allowed to cool, then diluted with Et2O (200 mL) and passed through a short Celite/silicaplug. The organic extracts were washed with NH4Cl (200 mL), H2O(200 mL) and brine (200 mL), dried over MgSO4, filtered and evaporated to give crude product as a yellow oil (2.65 g, 83%). The compound was taken on to the next stage without any further purification or characterisation. Method 3: To a dry flask was added methyl (2E)- 3-iodoprop-2-enoate (2.82 g, 13.3 mmol), Pd(OAc)2 (0.15 g, 0.67 mmol), P(o-tol)3(0.408 g, 1.34 mmol) and AgOAc (2.41 g, 14.4 mmol). The flask was purged with argon, and dry, degassed MeCN (72 mL) was added. 4,4,6-Trimethyl-2-vinyl-1,3,2-dioxaborinane (2.6 mL, 15 mmol) was then added, the vessel was purged further with argon, and the reaction mixture was then heated to 30 C with vigorous stirring for 19 h. The mixture was allowed to cool, then diluted with Et2O (200 mL) and passed through a short Celite/silica plug. The solvent was evaporated to give crude product as a yellow oil (2.84 g, 89%).The compound was taken on to the next stage without any further purification or characterisation. Method 4: To a dry flask was added methyl (2E)-3-iodoprop-2-enoate (1.0 g, 4.7 mmol), Pd(OAc)2 (0.011 g, 0.047 mmol), tri(2-furyl)phosphine (0.022 g, 0.094 mmol) and AgOAc (0.851 g, 5.11 mmol). The flask was purged with argon, and dry, degassed MeCN (28 mL) was added. 4,4,6-Trimethyl-2-vinyl-1,3,2-dioxaborinane (0.93 mL, 5.4 mmol) was then added, the vessel was purged further with argon, and the reaction mixture was stirred vigorously at room temperature for 3 days. The mixture was diluted with Et2O (71 mL) and passed through a short Celite/silica plug. The solvent was evaporated to give crude product as a pale yellow oil (1.18 g, 99%). The compound was taken on to the next stage without any further purification or characterisation.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (E)-Methyl 3-iodoacrylate, its application will become more common.

Reference:
Article; Madden, Katrina S.; Knowles, Jonathan P.; Whiting, Andrew; Tetrahedron; vol. 75; 45; (2019);,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com