Category: iodides-buliding-blocks

Application of 61203-48-3,Some common heterocyclic compound, 61203-48-3, name is 2-Iodo-4,5-dimethoxybenzoic acid, molecular formula is C9H9IO4, 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.

[C.] [N- (6-NITROQUINOLIN-4-YL)-N- (N, N-DIMETHYLAMINOETHYL)-2-IODO-5,] 6- dimethoxybenzamide (8c). Oxalyl chloride (1.5 g, 12.0 mmol) was added to a solution of 3, 4-dimethoxy-6-iodobenzoic acid (985 mg, 3.2 mmol) in anhydrous methylene chloride (20 mL), and the stirred mixture was refluxed for 3 hours. The mixture was then concentrated to dryness under reduced pressure. The acid chloride was redissolved in 20 mL of anhydrous methylene chloride, and this solution was added to a solution of 7c (700 mg, 2.7 mmol) and triethylamine (2.0 g, 20.0 mmol) in methylene chloride (30 mL), and the resulting mixture was stirred at reflux for 2 hours. The reaction mix was cooled and washed with saturated sodium bicarbonate (3 x 75 mL), and extracted with 5 % aqueous HCl (4 x 100 mL). The combined aqueous extracts were basified with 30% [NAOH] and then extracted with chloroform (3 x 100 mL). Combined organic extracts were then dried [(MGSO4)] and evaporated to give 1.15 g of the amide, in 78 % yield ; 1H NMR [(CDC13)] 8 2.23 (s, 6H), 2.63 (m, 2H), 3.35 (s, 3H), 3.71 (s, 3H), 3.96 [(M,] 1H), 4.29 (m, 1H), 6.50 (s, 1H), 6.94 (s, [1H),] 7.79 (d, 1H, [J=5.] 2), 8.22 (d, [1H,] [J=9.] 2), 8. 48 (d, 1H, J=9. 2), 9.0 (d, 1H, J=5. 2), 9.28 (s, [1H)] ; [13C] NMR [(CDC13)] [5] 45.5, 48.0, 55.6, 56.1, 56. 8, 82.3, 110.7, 120.9, 121.5, 122.9, 123.4, 125.5, 132.2, 133.7, 145.9, 148.4, 149.1, 149. 8, 151.5, 154.1, 169.7 ; IR (CHC13) 1345,1535, 1655.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Iodo-4,5-dimethoxybenzoic acid, its application will become more common.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY; LAVOIE, Edmond, J.; RUCHELMAN, Alexander, L.; LIU, Leroy, F.; WO2004/14906; (2004); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 20691-72-9, name is 4-Iodo-2-nitroaniline, 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 20691-72-9, Quality Control of 4-Iodo-2-nitroaniline

Method a To a solution of diphosgene (4.1 mL, 34.1 mmol) in EtOAc (40 mL) at 0 C. was added a solution of the 4-iodo-2-nitroaniline (45.5 mmol) in EtOAc (200-500 mL), and the mixture was heated to reflux for 18 h. The solvent was removed in vacuum to leave a brown solid, which was triturated with hot hexane (200 mL). The solid material was filtered off and the filtrate was concentrated under reduced pressure to leave the pure 4-iodo-2-nitrophenylisocyanate as a yellow solid.

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

Reference:
Patent; Hoffmann-La Roche Inc.; US6509328; (2003); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 83863-33-6, A common heterocyclic compound, 83863-33-6, name is 5-Iodo-2-methylaniline, molecular formula is C7H8IN, 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 solution of 5-iodo-2-methylaniline (1g, 42.91mmol) and 2-tert butyldicarbonate (1.03g, 47.19 mmol) in THF (10 ml) was stirred at reflux temperature for 2 hours. Solvent was then removed in vacuo, the residue dissolved in ethyl acetate and this solution was washed successively with 1M citric acid solution and brine. The organic phase was dried over MgSO4 and concentrated in vacuo. The resultant yellow-white solid was crystallized from hexane to give white solid 2 (1.22 g, 85.3%).

The synthetic route of 83863-33-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Raju, Gheevarghese; Capo, Joseph; Lichtenstein, Bruce R.; Cerda, Jose F.; Koder, Ronald L.; Tetrahedron Letters; vol. 53; 10; (2012); p. 1201 – 1203;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 3032-81-3, 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. 3032-81-3 name is 1,3-Dichloro-5-iodobenzene, 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.

8-Mercaptoadenine (3.6 mmol), neocuproine hydrate (0.36 mmol), Cul (0.36 mmol), NaO-?-Bu (7.2 mmol), 3,5-dichloro-iodobenzene (10.8 mmol), and anhydrous DMF (24 mL) were added to a round bottom flask flushed with nitrogen. The flask was sealed with Teflon tape and heated at 1 10 °C with stirring for 24-36 h under nitrogen. Solvent was removed under reduced pressure and the resulting residue was chromatographed (CH2Cl2:MeOH:AcOH, 20: 1 :0.5) to yield 15 as a yellow solid in 44 percent yield. -NMR (400 MHz, DMSO-i/6) delta 13.49 (IH, br s), 8.13 (IH, s), 7.59 (IH, s), 7.47 (2H, s), 7.36 (2H, br s); MS (ESI): m/z 312.1 [M + H+].

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dichloro-5-iodobenzene, and friends who are interested can also refer to it.

Reference:
Patent; MEMORIAL SLOAN-KETTERING CANCER CENTER; CHIOSIS, Gabriela; YAN, Pengrong; PATEL, Pallav; PATEL, Hardik J.; TALDONE, Tony; YANG, Chenghua; SUN, Weilin; OCHIANA, Stefan; WO2015/23976; (2015); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 97456-81-0, name is 1-Bromo-3-iodo-2-methylbenzene, 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 97456-81-0, Computed Properties of C7H6BrI

Step 3: preparation of (E)-methyl 4-(3-bromo-2-methylstyryl)-5-chloro-2-methoxybenzoate 1-Bromo-3-iodo-2-methylbenzene (616 mg, 2.07 mmol), methyl 5-chloro-2-methoxy-4-vinylbenzoate (470 mg, 2.07 mmol), Pd(Oac)2 (47 mg, 0.21 mmol), tri-o-tolylphosphine (126 mg, 0.415 mmol), Hunig’s Base (724 mul, 4.15 mmol), tetrabutylammonium chloride (576 mg, 2.07 mmol) were combined under N2 in acetonitrile (21 ml) at rt and warmed to 70 C. The reaction was stirred for 6 hr and then was concentrated, adsorbed onto diatomaceous earth (Celite) and was purified on silica gel (Biotage, 0-50% EtOAc/hexanes gradient over 10 CVs) to afford (E)-methyl 4-(3-bromo-2-methylstyryl)-5-chloro-2-methoxybenzoate (550 mg, 67% yield) as a yellow solid consistent by LCMS: M+H=396.80, Retention time=1.625 min, and NMR: 1H NMR (500 MHz, CHLOROFORM-d) delta 7.88 (s, 1H), 7.55 (t, J=8.1 Hz, 2H), 7.37-7.35 (m, 1H), 7.29 (s, 1H), 7.21 (s, 1H), 7.11 (t, J=7.9 Hz, 1H), 3.99 (s, 3H), 3.91 (s, 3H), 2.54 (s, 3H).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YEUNG, KAP-SUN; Connolly, Timothy P.; Frennesson, David B.; Grant-Young, Katharine A.; Hewawasam, Piyasena; Langley, David R.; Meng, Zhaoxing; Mull, Eric; Parcella, Kyle E.; Saulnier, Mark George; Sun, Li-Qiang; Wang, Alan Xiangdong; Xu, Ningning; Zhu, Juliang; Scola, Paul Michael; (511 pag.)US2017/107202; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 108078-14-4,Some common heterocyclic compound, 108078-14-4, name is 2-Iodo-3-methylbenzoic acid, molecular formula is C8H7IO2, 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.

EXAMPLE 131; 122 Dioxanel-d-Iodo-S-methyl-benzoylaminoHndan-l-carboxylic Acid Ethyl EsterA 10OmL round bottom flask is charged with 2-Iodo-3-methylbenzoic Acid (1.92g, 7.3 lmmol) and dry DCM (25mL). A stirring bar is added and stirring initiated. After 5min, HTBU (2.37g, 7.3 lmmol) is added. After 5min, the 2-amino-indane-2-carboxylic Acid Ethyl Ester (1.5Og, 7.31mmoles) is added followed by DIPEA (3.2mL, 18.37mmol). The reaction is allowed to stir for 118 hours. Analysis by tic of the reaction mixture (silica, 15% iPrOH/Dischloromethane) indicates complete consumption of the starting amine. The contents of the reaction flask are transferred to a separatory funnel and diluted with EtOAc (70 mL). This is washed with dilute aqueous HCl (3%, 2 x 3OmL), saturated aqueous NaHCO3 (2 x 3OmL) and brine (30 mL), dried over MgSO4, filtered and evaporated in vacuo to provide 2.04g of white solid. This material is dissolved in DCM (15mL). This material is purified utilizing an ISCO Companion with a 4Og cartridge of silica. The gradient is 10 % EtOAC in heptanes over 4 column volumes followed by a linear gradient to 50% EtOAc over 10 column volumes. 27mL fractions of UV active elutant were collected. Fractions 10 through 15 are combined and evaporated in vacuo to constant weight to give 2-(2-iodo-3-methyl- benzoylamino)-indan-2-carboxylic acid ethyl ester 1.04g of white solid.EXAMPLE 175; 149 l-d-Iodo-S-methyl-benzoylaminoHndane-l-carboxylic acid ethyl ester (175):A 10OmL round bottom flask is charged with 2-iodo-3-methylbenzoic acid (1.92g, 7.31mmol) and dry DCM (25mL). A stirring bar is added and stirring is initiated. After 5min, the HBTU (2.37g, 7.31mmol) is added. After 5min, the 2-amino-indane-2-carboxylic acid ethyl ester(1.5g, 7.31mmol) is added followed by N,N-diisopropylethyl-amine (3.2mL, 18.37mmol). The reaction is allowed to stir for 118h. Analysis by tic of the reaction mixture (silica, 15% iPrOH/DCM) indicates complete consumption of the starting amine. The contents of the reaction flask are transferred to a separatory funnel and diluted with EtOAc (7OmL). This is washed dilute aqueous HCl (3%, 2 x 3OmL), saturated aqueous NaHCO3 (2 X 3OmL) and brine (3OmL), dried over MgSO4, filtered and evaporated in vacuo to provide 2.04g of a white solid. This material is dissolved in 15mL of DCM. This material is purified utilizing an ISCO Companion with a 4Og cartridge of silica. The gradient is 10 % EtOAc in heptanes over 4 column volumes followed by a linear gradient to 50% EtOAc over 10 column volumes. 27mL fractions of UV active eluent are collected. Fractions 10 through 15 are combined and evaporated in vacuo. Pumping to constant weight gives 1.04g a white solid material.1H NMR (300 MHz, DMSO-d6): delta 1.20 (t, 3 H), 2.39 (s, 3 H), 3.52 (dd, 4H), 4.15 (q, 2H), 6.79 (d, IH), 6.97 (d, IH), 7.16 – 7.24 (m, 4H), 7.28 – 7.38 (m, 2H), 9.15 (s, IH). LC/MS m/z = 450.

The synthetic route of 108078-14-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; WO2008/151211; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 74-88-4,Some common heterocyclic compound, 74-88-4, name is Iodomethane, molecular formula is CH3I, 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: Following an adaptation of the procedure of McKillop et al.7, anaqueous solution of 1.20 g of NaOH (30 mmol, 3.0 eq.) in 50 mL of deionized water was added to astirring solution of 2.31 g (10 mmol) of 2-bromo-isovanillin (2-bromo-3-hydroxy-4-methoxybenzaldehyde)in 50 mL of dichloromethane. Next, phase transfer catalyst was added, as 3.40 g of eithertetrabutylammonium hydrogen sulfate (TBAHS, 10.0 mmol, 1.0 eq.) or recycled catalyst (assuming thatthe recovered catalyst is tetrabutylammonium hydroxide, 2.6 g is 10 mmol, 1.0 eq). Once dissolved, 17g (120 mmol, 12 eq.) of methyl iodide was then added to the mixture and the reaction was allowed tostir at room temperature. Reaction progress was monitored by HPLC. As monitored by HPLC, reactionprogress generally showed complete turnover to product with no side products by 3 hours, however thesolution was typically allowed to stir overnight for convenience. The reaction mixture was extracted with3 x 50 mL portions of CH2Cl2. The combined organic extracts were washed with brine and deionizedwater, dried over MgSO4, filtered, and concentrated by evaporation under reduced pressure to yield aeither a white or yellow solid. To remove catalyst, the solid was first ground to a fine powder with amortar and pestle. This solid was poured on top of a 2 – 3 cm layer of dry silica gel in a 3 – 4 cm (I.D.)sintered glass fritted Buchner funnel. The solid was extracted with 1:5 ethyl acetate:hexanes in 75 mLportions by pouring the solvent mixture over the dry solids with vacuum suction to collect the solutionin a round bottom flask. Allow the solids to dry between solvent portions for best separation. The first1250 mL typically contained 85 – 95% of pure product. The combined eluent was evaporated to drynessunder reduced pressure to afford a dense, white, flakey solid (2.06 g, 90%). If the product was found tocontain non-halogenated contaminants from the previous step, pure halogenated product was easilyobtained by recrystallization from hexanes. The phase transfer catalyst, presumably a mixture oftetrabutylammonium salts, was recovered by either scooping it out of the filter or by eluting with ethylacetate.

The synthetic route of 74-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Maresh, Justin J.; Ralko, Arthur A.; Speltz, Tom E.; Burke, James L.; Murphy, Casey M.; Gaskell, Zachary; Girel, Joann K.; Terranova, Erin; Richtscheidt, Conrad; Krzeszowiec, Mark; Synlett; vol. 25; 20; (2014); p. 2891 – 2894;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 10297-05-9,Some common heterocyclic compound, 10297-05-9, name is 1-Chloro-4-iodobutane, molecular formula is C4H8ClI, 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.

Example 23: 2-[5-Chloro-1-[(4-chlorophenyl)sulfonyl]pentyl]-1,4-difluorobenzene Under an argon atmosphere and at -78°C, n-butyl lithium (a 1.57M hexane solution, 3.52 ml) was added to a dimethoxyethane solution (30 ml) of the 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (1.52 g, 5.02 mmol) obtained in Example 5.. The temperature of the reaction mixture was elevated to room temperature, at which stirring was conducted for 15 minutes.. After cooling the reaction mixture to -78°C, 4-chloro-1-iodobutane (672 mul, 5.52 mmol) was added thereto and the mixture was stirred at room temperature for 24 hours.. A saturated ammonium chloride solution was added to the reaction mixture, followed by extraction with diethyl ether.. The extracts were combined, washed successively with water, a saturated aqueous solution of sodium thiosulfate and brine, dried over MgSO4, and then distilled under reduced pressure to remove the solvent.. The residue thus obtained was recrystallized from hexane, whereby the title compound (1.64 g, 83percent) was obtained as colorless needle crystals. IR (ATR) nu: 2945, 1583, 1495, 1475, 1311, 1277, 1230, 1149, 1142, 1082, 1014, 872, 822, 793, 752, 708, 629, 557, 532, 465 cm-1.1H-NMR (400MHz, CDCl3) delta: 1.33-1.48(2H,m), 1.72-1.87(2H,m), 2.08-2.18(1H,m), 2.43-2.52(1H,m), 3.44-3.53(2H,m), 4.52(1H,ddd,J=11.5,3.9,1.2Hz), 6.84(1H,td,J=9.0,4.4Hz), 6.96-7.02(1H,m), 7.23-7.28(1H,m), 7.39(2H,d,J=8.8Hz), 7.53(2H,d,J=8.8Hz). MS (m/z): 393 (M++H). Elemental Analysis for C17H16Cl2F2O2S Calculated: C 51.92percent; H 4.10percent; Cl 18.03percent; F 9.66percent; S 8.15percent. Found: C 51.33percent; H 4.07percent; Cl 17.64percent; F 9.72percent; S 8.25percent.

The synthetic route of 10297-05-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1466898; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 501433-06-3, name is 2,3-Difluoro-1,4-diiodobenzene, 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 501433-06-3, Product Details of 501433-06-3

General procedure: 1,2,3,4-Tetrahalobenzene (10 mmol), iron powder (0.89 equiv.),sulfur (0.66 equiv.) and NaSHnH2O (4.0 equiv.) were added to dryN,N-dimethylformamide (32 equiv.). The mixture was heated to 140 C for 16 h. The reaction mixture was cooled to room temperatureand added to water (50 mL). The mixture was filtered andair-dried to afford a black solid. The black solid was then addedto a solution of methanol (20 mL), ZnO (1.2 equiv.), NaOH(6.5 equiv.) and water (20 mL), and allowed to reflux for 2 h. Aftercooling to room temperature, the mixture was filtered with Celite.The filtrate was added to 2 M H2SO4 and then extracted withdichloromethane. The organic phase was washed with brine anddried with MgSO4. After filtration, evaporation and drying, the corresponding3,6-dihalo-1,2-benzenedithiol was afforded as a solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,3-Difluoro-1,4-diiodobenzene, and friends who are interested can also refer to it.

Reference:
Article; Tsukada, Satoru; Kondo, Masataka; Sato, Hironobu; Gunji, Takahiro; Polyhedron; vol. 117; (2016); p. 265 – 272;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 1258298-01-9,Some common heterocyclic compound, 1258298-01-9, name is 2,6-Dichloro-4-iodobenzoic acid, molecular formula is C7H3Cl2IO2, 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 solution of 2,6-dichloro-4-iodobenzoic acid (5.50 g, 17.4 mmol) in thionyl chloride (52 mL) was heated under reflux for 2 hours then diluted with toluene and concentrated under reduced pressure. The resultant residue was partitioned between EtOAc and saturated aqueous sodium bicarbonate solution. The organic layer was dried over Na2S04 and concentrated under reduced pressure to give the desired compound as a yellow oil (5.75 g, 99% yield). ¾ NMR (400 MHz, CDC13) delta 7.75 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,6-Dichloro-4-iodobenzoic acid, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLENCH, Toby; ELLWOOD, Charles; GOODACRE, Simon; LAI, Yingjie; LIANG, Jun; MACLEOD, Calum; MAGNUSON, Steven; TSUI, Vickie; WILLIAMS, Karen; ZHANG, Birong; WO2012/35039; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com