Category: iodides-buliding-blocks

56096-89-0, Name is 4-Fluoro-2-iodobenzoic acid, 56096-89-0, 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.

To 341 mg (1.24 mmo[) 4-f[uoro-2-iodobenzoic acid in 10 mL DMF were added 472mg (1.24 mmo[) HATU and 590 j.iL (3.40 mmo[) N,N-diisopropy[ethy[amine. Afterstirring for 5 minutes 300 mg (1.13 mmo[) methy[ 5-[(4-aminopheny[)carbamoy[]- 1H-imidazo[e-4-carboxy[ate (Intermediate 015) were added and the mixture was stirred for 8 hours at room temperature. The reaction was poured into water and the aqueous so[ution was extracted three times with DCM/2-propano[e (8:2). The combined organic [ayers were washed with sat. sodium carbonate so[ution and sat. sodiumch[oride so[ution. The organic phase was dried over sodium su[phate, andthe so[vent was removed under reduced pressure to afford the crude materia[ which was purified by f[ash co[umn chromatography to give 518 mg of the tit[e compound as a so[id materia[.

Statistics shows that 4-Fluoro-2-iodobenzoic acid is playing an increasingly important role. we look forward to future research findings about 56096-89-0.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERSTAFF, Jens; WAGNER, Sarah; BASTING, Daniel; GOLZ, Stefan; BENDER, Eckhard; LI, Volkhart Min-Jian; LIENAU, Philip; LIU, Ningshu; SIEGEL, Franziska; BAUSER, Marcus; SUeLZLE, Detlev; HOLTON, Simon; BAIRLEIN, Michaela; BUCHGRABER, Philipp; BALINT, Jozsef; WO2015/150449; (2015); A2;,
Iodide – Wikipedia,
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These common heterocyclic compound, 13194-68-8, name is 4-Iodo-2-methylaniline, 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. 13194-68-8

To a solution of 4-iodo-2-methyl-aniline (4.0 g, 17 mmol) and Pd(dppf)2Cl2 (140 mg, 0.17 mmol) in THF (50 mL) was added isopropylmagnisium chloride (25.5 mL, 51.0 mmol) at -78 C and was reacted at reflux for 4 h. The reaction was quenched with a saturated solution of NH4ci, extracted with EtOAc, dried over anhydrous Na2SC>4, filtered, and concentrated to dryness. The residue was purified by flash column chromatography to give the title compound as a brown solid (320 mg, 12%). MS (ESI): mass calcd. for ci0Hi5N, 149.1; m/z found, 150.0 [M+H]+.

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 13194-68-8.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ARORA, Nidhi; BACANI, Genesis M.; BARBAY, Joseph Kent; BEMBENEK, Scott D.; CAI, Min; CHEN, Wei; DECKHUT, Charlotte Pooley; EDWARDS, James P.; GHOSH, Brahmananda; HAO, Baoyu; KREUTTER, Kevin; LI, Gang; TICHENOR, Mark S.; VENABLE, Jennifer D.; WEI, Jianmei; WIENER, John J. M.; WU, Yao; ZHU, Yaoping; ZHANG, Feihuang; ZHANG, Zheng; XIAO, Kun; (1000 pag.)WO2017/100668; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A common heterocyclic compound, 2265-93-2, name is 2,4-Difluoroiodobenzene, 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. 2265-93-2.

[0255] 2-Prop-2-ynyl-2,3-dihydro-isoindol-l-one (50.0mg, 0.29mmol) was dissolved in triethylamine (2mL). To this was added Pd(PPh3)4 (13mg, 0.012mmol), Cul (6.7mg, 0.035mmol) and 2,4-difluoro-l-iodo-benzene (52.0uL, 0.438mmol) and the reaction was allowed to stir overnight. The solvent was evaporated and the residue was purified by prep. TLC (30% EtOAc/Hexanes) to afford the title compound (20.0mg, 24%) as a brown oil. XH NMR (300 MHz, CDC13): 5 7.90 (d, 1H), 7.45 (m, 4H), 6.84 (t, 2H), 4.72 (s, 2H), 4.59 (s, 2H).

The synthetic route of 2,4-Difluoroiodobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2006/20879; (2006); A1;,
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

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

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

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

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

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

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