Month: October 2020

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. 452-82-4, name is 1-Fluoro-2-iodo-4-methylbenzene, A new synthetic method of this compound is introduced below., 452-82-4

General procedure: A sealed tube equipped with a magnetic stir bar was charged with the corresponding 1-bromo -2-fluoro (or chloro) benzene/ 1-fluoro-2-iodobenzene (1 mmol), amino phenol (1 mmol), Pd(OAc)2 (5 mol%), xantphos (5 mol%) and DBU (2.5 mmol). The tube was purged with argon. Then DMF (10 V) was added followed by the addition of Co2(CO)8 (0.25 mmol). The tube was closed with seal plug instantly. The reaction tube was placed in a pre heated oil bath at 150 0C for 16 h. On completion, the reaction mixture was cooled to room temperature, added water and ethyl acetate (1:1). Precipitated solid was filtered through a Celite bed. The bed was washed thoroughly with ethyl acetate. Organic layer was separated. Aqueous layer extracted with EtOAc. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure and purified by flash column chromatography on silica gel (230-400 mesh) with ethyl acetate and petroleum ether as eluent to afford the corresponding dibenzoxazepinones.

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:
Article; Anchan, Kavitha; Baburajan, Poongavanam; Puttappa, Nagaswarupa H.; Kumar Sarkar, Sujit; Synthetic Communications; vol. 50; 3; (2020); p. 348 – 360;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 624-76-0

Add 7 mL of ethanol to the round bottom flask, then add 1.1 mL of 2-methylquinoline.Add 0.5mL of iodine solution,The reaction was heated to 50 C for 36 h, and after the reaction was completed, the reaction system was cooled to room temperature.Solid precipitated, filtered and washed with ethanolObtaining 1,2-dimethyl-quinoline iodide salt (Compound 2),The yield was 93%.Its nuclear magnetic resonance spectrum is shown in Figure 1.

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 624-76-0.

Reference:
Patent; University of Jinan; Lin Weiying; Sun Jie; Tian Minggang; (10 pag.)CN109851553; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

76801-93-9, A common heterocyclic compound, 76801-93-9, name is 5-Amino-N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide, molecular formula is C14H18I3N3O6, 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.

EXAMPLES EXAMPLE 1; Compound B was acetylated in a mixture of acetic anhydride and acetic acid in the presence of catalytic amounts of p-toluene sulphonic acid at 50-125C. Excess acetic anhydride and acetic acid was distilled off under reduced pressure, and the reaction mixture was diluted with methanol and water. The resulting reaction mixture had the following composition: Overacetylated Compound A (a mixture of compounds with varying number of acetyl groups attached): 97.7-98.3 % by area in HPLC Compound B: 0.0-0.3 % by area in HPLC Concentration: 31 w/v % Compound A in an approximately 2.5:1 methanol/water mixture Conductivity: 5.1-5.7 mS/cm Compound B was produced from the reaction mixture in a system according to Figure 1. The reaction mixture from the acetylation reaction (prepared batch wise) was fed into the static mixer in a flow ratio of 1.04 mL reaction mixture: 1.0 mL 20 w/w % NaOH at about 55C (outlet temperature). The absolute feeding rate of the reaction mixture was 2.6 kg/hour. The pH was kept at about 12.2 at steady state. HPLC of the output stream showed Compound A in 98.2 % purity with 0.23 % Compound B present at steady state. The continuous crystallisation was performed as described above. The pH in the first and second crystalliser varied between 11.1 and 11.5 over time, while the pH in the third and fourth crystalliser varied between 6.2 and 7.2. The temperature was 60C in the two first crystallisers and 20C in the third and fourth. Residence times were held at 2, 2, 2 and 8 hours, respectively. 20 % of the mother liquor volume was stripped off in the third crystalliser at a pressure of 240-250 mbar. The water content in the methanolic distillate from the stripping was 34-35 w/w %. The resulting slurry from the fourth crystalliser was transferred to a holding tank before filtration. The slurry was filtered in a continuous rotation filter at 1.6-3.2 barA. The filtration rate varied between about 500 and 900 L/m2/hour (about 500-650 L/m2/hour at steady state). The filter cake was washed with methanol (about 1.9 kg/kg Compound A) in the same filter. The resulting salt content in the filter cake was 0.2-0.3 w/w % NaCl. The moist filter cake was dried in a continuous fluid bed (spin flash) dryer at 120-130C gas temperature. The maximum temperature exposed to the product was 80C. The resulting moisture content was 0.4 w/w %. The purity of dry Compound A in HPLC was 99.5 % by area.

The synthetic route of 76801-93-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GE Healthcare AS; EP2281811; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 124700-41-0, name is 2-Fluoro-5-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. 124700-41-0

A stirred suspension of 2-fluoro-5-iodobenzoic acid (99.7 g) in DCM (1 L) at 20 C. was treated with oxalyl chloride (49.8 mL) and DMF (0.3 mL). After 3 h further DMF (0.1 mL) was added. After a further 2 h the clear solution was evaporated and re-evaporated from toluene (3¡Á200 mL). The acid chloride was re-dissolved in toluene (1.5 L) and treated with triethylamine (79.2 mL) and ethyl 3-(dimethylamino)acrylate (65.3 g). After stirring for 2.5 h at 90 C. the mixture was filtered and evaporated. The residue was redissolved in EtOAc, washed with saturated sodium hydrogen carbonate solution (2¡Á), water, saturated brine, dried (MgSO4) and treated with decolourising charcoal for 0.5 h. The mixture was filtered, evaporated, redissolved in diethyl ether and allowed to crystallise. The solid was filtered off, washed with diethyl ether and dried to give the title compound (91.2 g). On concentration and seeding a second crop was obtained (9.0 g); ESMS m/z 391.9 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 124700-41-0, its application will become more common.

Reference:
Patent; Glaxo Group Limited; US2008/269146; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

672-57-1, 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. 672-57-1, name is 1-Chloro-2-iodo-4-(trifluoromethyl)benzene, A new synthetic method of this compound is introduced below.

1 4-(2-Chloro-5-trifluoromethylphenyl)-1-fluoro-2-fluoromethyl-3-butyn-2-ol A mixture of 4-chloro-3-iodobenzotrifluoride (63.3 g), 1-fluoro-2-fluoromethyl-3-butyn-2-ol (28.8 g), triethylamine (26.2 g), cuprous iodide (0.38 g), bis(triphenylphosphine)palladium chloride (1.40 g) and N,N-dimethylformamide (100 ml) was stirred under a nitrogen atmosphere under heating at 80 C. for 1.5 hours. To the reaction mixture, 2 N HCl and a hexane/ethyl acetate mixed solvent (3/1) were added and the insoluble matter was filtered off with Celite; following extraction with a hexane/ethyl acetate mixed solvent (3/1), the resulting organic layers were combined, washed with a saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate and concentrated under reduced pressure; the resulting residue was purified by distillation to give 4-(2-chloro-5-trifluoromethylphenyl)-1-fluoro-2-fluoromethyl-3-butyn-2-ol (44.5 g) having a boiling point of 105-107 C./1 mmHg. 1H-NMR (CDCl3) delta: 2.70-3.00(1H, m), 4.52-4.71(4H, m), 7.54-7.56(2H, m), 7.76(1H, t, J=0.7 Hz)

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; Chugai Seiyaku Kabushiki Kaisha; US6455708; (2002); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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.

General procedure: 2-Phenylimidazo[1,2-a]pyrazine 2 (1.0 mmol) was introducedinto a 10 mL vial with (hetero)arylhalide (2.0 mmol), palladiumacetate (0.04 mmol), tricyclohexylphosphine tetrafluoroborate(0.08 mmol), pivalic acid (0.6 mmol) and potassium carbonate(3.0 mmol) in N,N-dimethylacetamide (4 mL). The vial was purgedwith argon for 10 min and then sealed. The mixture was heated at100 C for 18e40 h and then it was cooled to room temperature.Water was added and the aqueous layer was extracted with ethylacetate (2 x 10 mL). The combined organic extracts were washedwith brine and water, dried over sodium sulfate, filtered, concentratedin vacuo and purified by silica gel column chromatography.Trituration with diisopropylic ether afforded the compounds 4aeg.

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 3032-81-3.

Reference:
Article; Marchand, Pascal; Bazin, Marc-Antoine; Pagniez, Fabrice; Riviere, Guillaume; Bodero, Lizeth; Marhadour, Sophie; Nourrisson, Marie-Renee; Picot, Carine; Ruchaud, Sandrine; Bach, Stephane; Baratte, Blandine; Sauvain, Michel; Pareja, Denis Castillo; Vaisberg, Abraham J.; Le Pape, Patrice; European Journal of Medicinal Chemistry; vol. 103; (2015); p. 381 – 395;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

628-21-7, Adding a certain compound to certain chemical reactions, such as: 628-21-7, name is 1,4-Diiodobutane, 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 628-21-7.

To a solution of 500 mg (2.16 mmol) of L-serine benzyl ester hydrochloride and 869 mg (2.81 mmol, 1.3 eq.) of 1,4-diiodobutane in 25 ml of 2-propanol were added, under argon at RT, 595 mg (5.61 mmol, 2.6 eq.) of sodium carbonate and the mixture was stirred at 90 C. overnight. After cooling to RT and removal of the 2-propanol under reduced pressure, the residue was admixed with ethyl acetate. The insoluble salts were filtered off. The filtrate was washed with water and the organic phase was dried (sodium sulphate), filtered and concentrated under reduced pressure. The residue was purified by means of flash chromatography (silica gel 50, dichloromethane, then dichloromethane/methanol 5:1). Yield: 268 mg (48% of theory) LC/MS [Method 5]: Rt=2.03 min; MS (ESIpos): m/z=250 (M+H)+.

According to the analysis of related databases, 628-21-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ROeHRIG, Susanne; HILLISCH, Alexander; HEITMEIER, Stefan; SCHMIDT, Martina Victoria; SCHLEMMER, Karl-Heinz; TERSTEEGEN, Adrian; TELLER, Henrik; US2018/346424; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

64248-58-4, A common heterocyclic compound, 64248-58-4, name is 1,2-Difluoro-4-iodobenzene, molecular formula is C6H3F2I, 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: A solution of Pd(OAc)2 (11.2 mg, 0.05 mmol) and Ph3As (67.5 mg, 0.22 mmol) in dry DMF (3 mL) was stirred in a Schlenk flask under nitrogen atmosphere at 65 C for 15 min to form the catalyst complex. Then, aryl iodide (3.00 mmol), compound 5 (437 mg, 1.00 mmol), Et3N (708 mg, 7.00 mmol), and HCOOH (0.226 mL, 6.00 mmol) were added. The mixture was heated to 65 C for 24-48 h. After cooling to room temperature, brine (50 mL) was added, and the mixture was extracted with AcOEt. The aqueous layer was dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography or flash chromatography.

The synthetic route of 64248-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Albayrak, Fatma; Gunkara, Omer Tahir; Ersoy, Elif Basak; Ocal, Nuket; Kaufmann, Dieter E.; Arkivoc; vol. 2017; 5; (2017); p. 244 – 256;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 624-75-9, name is 2-Iodoacetonitrile, molecular formula is C2H2IN, 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. 624-75-9

To a solution of iodoacetonitrile 11 (0.16?mL, 2.10?mmol) and N-Boc piperidinone 9 (398?mg, 2.0?mmol) in THF was added i-PrMgBr (3.0?N in THF, 0.7?mL, 2.10?mmol) at -78?C under an Argon atmosphere. After being stirred for 2?h, the reaction was quenched with saturated aqueous NH4Cl solution (5.0?mL) and extracted with ethyl acetate (3?*?5.0?mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified on silica gel (eluent: EtOAc/n-hexane?=?1:2) to give the ketoamide 12 in 88% yield as a light yellow wax. IR (film) numax: 3362, 2977, 2921, 2260, 1729, 1698, 1519, 1454, 1392, 1366, 1273, 1251, 1170, 1058, 1009?cm-1; 1H NMR (400?MHz, CDCl3) delta 1.44 (s, 9H), 1.47-1.57 (m, 2H), 1.57-1.73 (m, 2H), 2.65 (t, J?=?7.1?Hz, 2H), 3.02-3.21 (m, 2H), 3.49 (s, 2H), 4.63 (s br, 1H); 13C NMR (100?MHz, CDCl3) delta 20.2, 28.3, 29.2, 31.9, 39.8, 41.5, 79.2, 113.7, 156.0, 197.3; HRMS calcd for [C12H20N2NaO3]+ (M + Na+): 263.1366; found: 263.1365.

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

Reference:
Article; Cheng, Jiang-Tao; Zheng, Xiao; Huang, Pei-Qiang; Tetrahedron; vol. 75; 12; (2019); p. 1612 – 1623;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 914225-70-0, name is 1-(5-Fluoro-2-iodophenyl)ethanone, 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 914225-70-0, 914225-70-0

Step 1 : A solution of (-)-DIPCI (57.1 g, 178 mmol) in THF (100 ml) was cooled to -20 to -30 C. A solution of compound 1 (31 .3 g, 1 19 mmol) in THF (100 ml) was then added dropwise, via addition funnel (30 min addition). The reaction was left to warm up to RT. After 2 h, the reaction was cooled to -30 C and another portion of (-)-DIPCI (38.0 g, 1 19 mmol) was added. After 30 min, the reaction was allowed to warm to RT and after 1 h, the solvents were removed in vacuo and the residue re-dissolved in MTBE (200 ml). A solution of diethanolamine (31 g, 296 mmol) in ethanol/THF (15 ml/30 ml) was added via addition funnel, to the reaction mixture under an ice bath. The formation of a white precipitate was observed. The suspension was heated at reflux for 2 hours then cooled to room temperature, filtered and the mother liquids concentrated in vacuo. The residue was suspended in heptane/EtOAc (7:3, 200 ml) and again filtered. This procedure was repeated until no more solids could be observed after the liquids were concentrated. The final yellow oil was purified by column chromatography (eluent: cyclohexane/EtOAc- 99:1 to 96:4). The resulting colorless oil was further purified by recrystallisation from heptanes, to give alcohol compound 2 (25 g, 80% yield, 99% purity and 96% ee) as white crystals. 1H NMR (400 MHz, CDCI3) delta 7.73 (dd, 1 H), 7.32 (dd, 1 H), 6.74 (ddd, 1 H), 4.99 – 5.04 (m, 1 H), 2.01 (d, 1 H), 1.44 (d, 3 H). LCMS-ES: No ionization, Purity 99%. Chiral GC (column CP-Chirasil-DexnCB): 96% ee; Rt (minor) 17.7 minutes and Rt (major) 19.4 minutes.

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-(5-Fluoro-2-iodophenyl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; BAILEY, Simon; BURKE, Benjamin, Joseph; COLLINS, Michael, Raymond; CUI, Jingrong, Jean; DEAL, Judith, Gail; HOFFMAN, Robert, Louis; HUANG, Qinhua; JOHNSON, Ted, William; KANIA, Robert, Steven; KATH, John, Charles; LE, Phuong, Thi, Quy; MCTIGUE, Michele, Ann; PALMER, Cynthia, Louise; RICHARDSON, Paul, Francis; SACH, Neal, William; WO2013/132376; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com