Category: iodides-buliding-blocks

Some common heterocyclic compound, 116632-39-4, name is 5-Bromo-2-iodotoluene, molecular formula is C7H6BrI, 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. category: iodides-buliding-blocks

General procedure: (R)-(4-bromo-2-methylphenyl)((2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6- ((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methanol (101R) and (S)-(4-bromo-2- methylphenyl)((2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6- ((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methanol (101S). Synthesis B: Into a flask containing 4-bromo-1-iodo-2-methylbenzene (22.6 g, 76.1 mmol) in anhydrous Et2O (200 mL) under N2, was added n-BuLi/Hexanes (2.5 M, 26 mL, 65.23 mmol) dropwise at -78 C. After 1 h, the freshly prepared crude 2,3,4,6-Tetra-O-benzyl-alpha-D-mannopyranosyl carbaldehyde (12.0 g, 21.74 mmol) dissolved in Et2O (90 mL) was added via cannula over a period of 5 minutes. The mixture was stirred at -78 C for 30 min, and then slowly warmed to 0 C over a period of 1.5 h. The reaction mixture was quenched with saturated aq. NH4Cl and extracted with EtOAc (250 mL x 3). The combined organic phase was washed with brine (100 mL), dried over Na2SO4 and filtered .The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography (phase A: PE, phase B: CH2Cl2 / EtOAc / PE (20/1/2)) to give the 101R (4.0 g, 26% yield for two steps) as light yellow oil and 101S (8.0 g, 51% yield for two steps) as light yellow oil. Formula: C42H43BrO6 Exact Mass: 722.22 Molecular Weight: 723.69 Analytical data for Intermediate 101R: 1H NMR (300 MHz, CDCl3) delta 7.41-7.28 (m, 21H), 7.18-7.13 (m, 2H), 5.08 (d, J = 5.1 Hz, 1H), 4.71(2d, J = 11.7 Hz, 1H), 4.64-4.56 (m, 3H), 4.49 (s, 2H), 4.40 (s, 2H), 4.28 – 4.21(2m, 1H), 4.18 – 4.13 (m, 1H), 4.10 (t, J = 5.1 Hz, 1H), 3.99-3.94 (m, 1H), 3.89 (t, J = 5.9 Hz, 1H), 3.83-3.70 (m, 2H), 3.49 (br. s., 1H), 2.29 (s, 3H). ESI-MS [M+Na+] calcd for (C42H43BrO6Na) found: 745.5 (100%), 747.5 (97.3%). Formula: C42H43BrO6 Exact Mass: 722.22 Molecular Weight: 723.69 Analytical data for Intermediate 101S: 1H NMR (300 MHz, CDCl3) delta 7.37 – 7.16 (m, 23H), 5.06 (d, J=5.5 Hz, 1H), 4.73 – 4.67 (m, 1H), 4.62 – 4.44 (m, 7H), 4.11 – 4.03 (m, 2H), 3.85 – 3.76 (m, 3H), 3.73 – 3.67 (m, 2H), 3.19 (br. s., 1H), 2.18 (s, 3H). ESI-MS [M+Na]+ calcd for C42H43BrO6Na+ 745.21, found 745.5 (100%), 747.5 (97.3%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 116632-39-4, its application will become more common.

Reference:
Patent; FIMBRION THERAPEUTICS, INC.; JANETKA, James, W.; MYDOCK-MCGRANE, Laurel; (136 pag.)WO2017/156508; (2017); 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. 916792-62-6, name is 3-Fluoro-2-iodobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 916792-62-6

2-lodo-4- fluorobenzonitrile (2.5 g, 10.3 mmol) and 2-tributylstannane pyrimidine (3.7g, 10.0 mmol) were combined and dissolved in degassed DME (18 ml) then purged with bubbling N2 for 5 minutes. The reaction was treated withPd(PPh3) (577 mg, 0.5 mmol) and then purged with bubbling for 5 minutes in a sealed vessel and then heated in microwave at 160 C for 90 min. The reaction was cooled and filtered through celite and concentrated to minimum volume and the ppt the formed was diluted with hexanes (40 ml) and cooled to 0 C then filtered. The solid purified (FCC) (20-100% EA / hex) to give 3-fluoro- 2-(pyrimidin-2-yl)benzonitrile. 1 H NMR (400 MHz, CDCI3): 8.93 (d, J = 4.9 Hz, 2H), 8.14 (dd, J = 9.6, 2.7 Hz, 1 H), 7.86 (dd, J = 8.6, 5.3 Hz, 1 H), 7.36 (t, J = 4.9 Hz, 1 H), 7.32 – 7.24 (m, 1 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 916792-62-6.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50200; (2011); 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. 40400-15-5, name is 2-(2-Iodophenyl)acetonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C8H6IN

2-(2-iodophenyl)acetonitrile (1.3 mL, 10 mmol) was dissolved in DMF (20 mL), and the solution was cooled to 0 C. NaH (1.0 g, 26 mmol) 60% suspension in mineral oil was added to the solution in portions, and the mixture was heated at 60 C for 1.5 hours. tert-Butyl bis(2-chloroethyl)carbamate (3.0 g, 12 mmol) was added to the reaction, and the mixture was stirred at 60 C for 2 hours. The reaction was cooled down to room temperature, brine (25 mL) was added, and the mixture was extracted with EtOAc (3 X 100 mL). The combined organic layers were washed with brine, dried and evaporated to give a residue, which was purified with flash chromatography (EtOAc/hex 5-70%). The second eluting peak was collected to provide tert-butyl 4-(2-iodophenyl)-4-cyanopiperidine-1-carboxylate (1.8 g, 4.9 mmol, 48 % yield) as an oil. m/z (esi/APCI) M+1 =413.

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; ARRAY BIOPHARMA INC.; BLAKE, James F.; BOYS, Mark Laurence; CHICARELLI, Mark Joseph; COOK, Adam; ELSAYED, Mohamed S. A.; FELL, Jay B.; FISCHER, John P.; HINKLIN, Ronald Jay; MCNULTY, Oren T.; MEJIA, Macedonio J.; RODRIGUEZ, Martha E.; WONG, Christina E.; (259 pag.)WO2020/81848; (2020); 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. 460-37-7, name is 1,1,1-Trifluoro-3-iodopropane, A new synthetic method of this compound is introduced below., category: iodides-buliding-blocks

5.0 g (21.0 mmol) of the compound from Ex. 165A and 7.25 g (52.5 mmol) of potassium carbonate were stirred in a mixture of 95 ml acetonitrile and 15 ml of DMF at RT for 15 before 14.1 g (63.0 mmol) 1,1,1-trifluoro-3-iodopropane added .The reaction mixture was stirred at a temperature of 78 C for about 16 h.After cooling to RT was diluted with 500 ml ethyl acetate and washed successively twice with 100 ml of water and once with 50 ml of saturated sodium chloride solution.After drying over anhydrous sodium sulfate, was filtered and the filtrate concentrated to dryness.The crude product was purified by chromatography (80 g silica gel, eluent: heptane / ethyl acetate 100: 0-> 60:40).After concentrating the product fractions and drying the residue 2.99 g (42% d. Th.) The title compound obtained.

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; BAYER PHARMA AKTIENGESELLSCHAFT; HAERTER, MICHAEL; DELBECK, MARTINA; KALTHOF, BERND; LUSTIG, KLEMENS; LINDNER, NIELS; KAST, RAIMUND; WASNAIRE, PIERRE; SUESSMEIER, FRANK; (372 pag.)TW2016/7950; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 128140-82-9, A common heterocyclic compound, 128140-82-9, name is 1-(Difluoromethoxy)-4-iodobenzene, molecular formula is C7H5F2IO, 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.

Step 7) 4-[5-(4-Difluoromethoxy-phenylethynyl)-2-fluoro-phenyl]-butyronitrile To a solution of 1-Difluoromethoxy-4-iodo-benzene (0.21 g, 0.79 mmol) in DMF (3.5 ml) were added TEA (0.55 mL, 57.4 mmol) and 4-(5-Ethynyl-2-fluoro-phenyl)-butyronitrile (0.48 g, 0.79 mmol). The reaction was degassed by bubbling argon through it for 5 min and then dichlorbis(triphenylphospine)palladium (0.0.28 g, 0.04 mmol), and copper iodide (0.008 g, 0.57 mmol) were added simultaneously. The reaction mixture was heated at 65 C. for 15 min. cooled and quenched with 0.1 N HCl (10 ml). The aqueous layer was extracted with Et2O (3*10 ml). The combined organic extracts were washed with brine (25 ml), dried (MgSO4), and concentrated. The crude material was purified by silica gel chromatography (10-20% Ethyl acetate/Petroleum Ether) to afford the titled compound (0.235 g, 90%) as a brown oil that solidified on standing, and was identified by NMR and mass spectral analyses. MS (EI+): 329 (M+).

The synthetic route of 128140-82-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH; US2009/48320; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 61272-76-2, The chemical industry reduces the impact on the environment during synthesis 61272-76-2, name is 4-Fluoro-2-iodoaniline, I believe this compound will play a more active role in future production and life.

To the reaction tube was added 0.50 mmol (0 ? 1185 g) of 4-fluoro-2-iodoaniline, 0 · 25mmol (0 0600g) of the nine Water sodium sulfide, 2 mL of N, N-dimethylformamide and 1.50 mmol (0.1142 g) of carbon disulfide were added under an inert gas atmosphere and the reaction was stirred at 110 ° C for 12 hours, After the reaction was complete, the reaction solution was cooled to room temperature, and 3 mL of 4N hydrochloric acid was added for 15 min. The reaction solution was extracted three times with methylene chloride. The organic phases were combined and dried over anhydrous magnesium sulfate for 2 hours. And finally the crude dichloromethane solvent was distilled off under reduced pressure to give the crude product. The crude product was subjected to column chromatography (200-300 mesh silica gel) eluting with a petroleum ether and ethyl acetate (8: 1-2: 1) to give a white powder having a purity of more than 99percent Thiobenzothiazole 40.6 mg, the isolated yield was 43.8percent.

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-Fluoro-2-iodoaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Inner Mongolia University of Technology; Zhu, Ning; Qin, weijing; Hong, HaiLong; Han, LiMing; Jie, ruijun; (8 pag.)CN104098529; (2016); B;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 628-77-3, 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. 628-77-3, name is 1,5-Diiodopentane, This compound has unique chemical properties. The synthetic route is as follows.

Example 15 (n=5); (a) 1, 1″- [ (Pentane-1, 5-diyl) dioxyjbisf (11S, llaS)-10- (tert- butyloxycarbonyl)-7-methoxy-11- (tetrahydro-pyran-2-yloxy)- 1, 2, 3, 10, 11, 11a-hexahydro-5H-pyrrolo [2, 1-c] [1, 4] benzodiazepine-5- one] (15c); 1,5-Diiodopentane (72.2 mg, 0.22 mmol, 0.5 equiv) was added to the mixture of monomer 14 (0.2 g, 0.44 mmol, 1.0 equiv) and potassium carbonate (0.98 mmol, 2.2 equiv) in dry DMF (30 mL), and the resulting mixture was heated to 90C under a nitrogen atmosphere for 5 h. Removal of excess solvent under reduced pressure afforded a crude solid, which was subjected to flash column chromatography (SiO2, 50% EtOAc-hexane) to afford the dimerized compound 15c (212 mg, 0.21 mmol, 98% yield, mixture of diastereomers from THP protecting group) as a solid: [a] 20D = +40 (c = 0.22, CHCl3) ; 1H NMR (CDC13, 400 MHz) : 5 1. 21-1. 83 (m, 64H, 14-H, Boc, THP), 1. 88-2. 18 (m, 24H, 1-H, 2-H, 13-H), 3.41-3. 73 (m, 16H, 3-H, 11a-H, THP), 3.84-4. 10 (m, 24H, 12-H, 7-OMe, THP), 4.97-5. 15 (m, 4H, THP), 5.66-5. 75 (d, 2H, 11-H), 5.77-5. 89 (d, 2H, 11-H), 6.50 (s, 2H, 9- H), 6.84 (s, 2H, 9-H), 7.17 (s, 2H, 6-H), 7.21 (s, 2H, 6-H); 13C NMR (CDCl3, 400 MHz): 6 19.9, 20.5, 21.0, 22.7, 23. 1, 23.3, 25.3, 28. 1, 28.2, 28.9, 29.1, 31.0, 31.3, 46.3, 56.0, 56.1, 60.0, 60.1, 63.4, 64.6, 68.7, 69. 0, 80. 9, 81. 3, 88.2, 91.2, 95.7, 100.4, 110.2, 110.7, 114.5, 115.0, 126.3, 129. 7, 129. 8, 148.5, 148.8, 150.0, 155.1, 167.4, 167.6 ; IR (neat): 3431,2945, 1704, 1643, 1604,1513, 1453, 1432, 1327,1271, 1202,1163, 1023cm-1 ; MS (FAB) m/z (relative intensity) 987 ([M + Na]+., 37), 965 (M +., 100), 763 (92), 863 (75), 982 (49).

The chemical industry reduces the impact on the environment during synthesis 1,5-Diiodopentane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SPIROGEN LIMITED; WO2005/85259; (2005); A2;,
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. 2265-91-0, name is 1,3-Difluoro-5-iodobenzene, A new synthetic method of this compound is introduced below., Safety of 1,3-Difluoro-5-iodobenzene

PotassI.um phosphate (1.9 g, 8.7 mmol), trI.s(dI.benzylI.deneacetone)dI.palladI.um (0.27 g, 0.29 mmol), Xantphos (0.17 g, 0.29 mmol) and 3,5-dI.fluoroI.odobenzene (1.5 g, 6.4 mmol) were addedsuccessI.vely to a mI.xture of ethyl 2-aminothI.azole-4-carboxylate (1.0 g, 5.8 mmol) I.n a mI.xture of 9 ml of toluene and 3 ml of water. The mI.xture was flushed wI.th argon for 20 mins, then heated I.n the mI.crowave to 140 C for 1 h. The reactI.on mI.xture was dI.luted wI.th water and extracted wI.th ethyl acetate. The organI.c layer was washed wI.th saturated aqueous sodI.um bI.carbonate solutI.on and water, drI.ed over magnesI.um sulfate and evaporated under reduced pressure. The resI.due was purI.fI.ed bychromatography on sI.lI.ca gel, usI.ng ethyl acetate and cyclohexane as eluents, to delI.ver ethyl 2-(3,5- dI.fluoroanI.lI.no)thI.azole-4-carboxylate (0.16 g, 0.56 mmol). 1H-NMR (400 MHz, CDCl3): oe = 1.41 (t, 3H), 4.40 (q, 2H), 6.54 (t, 1H), 6.95 (d, 2H), 7.63 (s, 1H)

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; SYNGENTA PARTICIPATIONS AG; JEANMART, Stephane, Andre, Marie; ZAMBACH, Werner; RENDINE, Stefano; LAMBERTH, Clemens; BEAUDEGNIES, Renaud; POULIOT, Martin; BONVALOT, Damien; (73 pag.)WO2017/207362; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 450412-29-0, name is 1-Bromo-3-fluoro-2-iodobenzene, 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 450412-29-0, Computed Properties of C6H3BrFI

Bromo-3-fluoro-2-iodobenzene (100 g, 333.5 mmol),5-Chloro-2-methoxyphenylboronic acid (62.2 g, 333.5 mmol) was dissolved in tetrahydrofuran (800 mL). To this was added a 2 M solution of sodium carbonate (500 mL)Tetrakis (triphenylphosphine) palladium (0) [Pd (PPh3) 4] (7.7 g, 6.7 mmol) was added and refluxed for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, and the resulting mixture was extracted three times with water and toluene.The toluene layer was separated and dried over magnesium sulfate. The filtrate was distilled under reduced pressure, and the resulting mixture was recrystallized three times using chloroform and ethanol to obtain Compound A-1 (53.7 g, yield 51%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3-fluoro-2-iodobenzene, and friends who are interested can also refer to it.

Reference:
Patent; LG Chem, Ltd.; Jeong Min-u; Lee Dong-hun; Huh Jeong-o; Jang Bun-jae; Huh Dong-uk; Han Mi-yeon; (48 pag.)KR2018/61075; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 7681-82-5,Some common heterocyclic compound, 7681-82-5, name is Sodium iodide, molecular formula is INa, 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.

To a solution of complex [Pd(P,P)Cl2] (100 mg, 0.138 mmol) in10 mL of acetone, were added 207 mg of NuaI (1.380 mmol), underinert atmosphere and vigorous stirring. The dark yellow solutionwas stirred at room temperature for 2 h. After acetone wascompletely removed under vacuum, 10 mL of CH2Cl2 were addedto the resulting solid. The mixture was filtered in order to removethe inorganic salts. Subsequent addition of n-hexane (20 mL) to thefiltrate led to the formation of a yellow solid, which was filteredand dried under vacuum. Yield: 103 mg, 82%. HRMS (positiveESI-MS, Fig. S1, Supplementary Material): calcd for C30H35I2NNaO3P2PdSi [M+Na]+ 929.8878, found 929.8898; calcd forC30H35I2KNO3P2PdSi [M+K]+ 945.8617, found 945.8634. IR (KBr,cm1): 513 (s), 558 (m), 693 (s), 741 (s), 869 (s), 1098 (s), 1430(s), 2820 (w), 2931 (w). 1H NMR (300 MHz, CDCl3): d 0.20 (t, 2H,Si-CH2), 1.20 (m, 2H, -CH2-CH2-Si), 1.60, 2.80 (m, 2H, N-CH2),3.40 (s, 9H, Si-OCH3), 7.30, 7.4-8.0 (m, 20H, Harom). 31P NMR(121.5 MHz, CDCl3): d 24.2. UV-Vis (CH2Cl2), [k (nm), e (M1cm1)]: (418, 6800), (292, 23000), (263, 26150).

The synthetic route of 7681-82-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Stamatopoulos, Ioannis K.; Kapsi, Maria; Roulia, Maria; Vougioukalakis, Georgios C.; Raptopoulou, Catherine P.; Psycharis, Vassilis; Kostas, Ioannis D.; Kollar, Laszlo; Kyritsis, Panayotis; Polyhedron; vol. 151; (2018); p. 292 – 298;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com