Month: April 2021

Some common heterocyclic compound, 112671-42-8, name is 4-Bromo-1-iodo-2-nitrobenzene, molecular formula is C6H3BrINO2, 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. Recommanded Product: 112671-42-8

Intermediate M1-a (3.7 g, 18.6 mmol)With 2-iodo-5-bromonitrobenzene (15.3 g, 46.7 mmol),Sodium tert-butoxide (7.1g, 74.4mmol), toluene 100mL,Nitrogen protection, Pd2(dba)3(0.3g),Tri-tert-butylphosphine (20ml, 10% toluene solution), stirring turned on,Heated to 100 C reflux, reaction 12h, the reaction solution washed,The organic phase was concentrated and passed through a silica gel column. The eluent was petroleum ether:Ethyl acetate = 50:1, concentrated rinse,Obtain the intermediate M1-b(9.2g, yield 82.7%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 112671-42-8, its application will become more common.

Reference:
Patent; Beijing Dingcai Technology Co., Ltd.; Gu’an Dingcai Technology Co., Ltd.; Fan Hongtao; Xing Qifeng; Zhang Wei; Zhang Xianghui; (28 pag.)CN107880050; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 263351-43-5,Some common heterocyclic compound, 263351-43-5, name is tert-Butyl 3-iodobenzylcarbamate, molecular formula is C12H16INO2, 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 the product of preparation 49 (0.75 g, 2.25 mmol), 4-hydroxy phenylboronic acid (0.62 g, 4.50 mmol) and 1, 1′- bis (diphenylphosphino) ferrocenyl palladium (II) chloride (0.11 g, 0.14 mrnol) in N, N-dimethylformamide (14 mL) was treated with 2M aqueous sodium carbonate solution (4 mL) and the resulting mixture was heated at 80 C for 16 hours. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel, eluting with ethyl acetate: pentane, 25: 75, to afford the title compound as a pale pink crystalline solid in quantitative yield, 0. 73 g. ‘H NMR (400MHz, CDCI3) 8 : 1.47 (9H, s), 4. 33-4. 41 (2H, m), 4. 87-4. 94 (1H, bs), 6.89 (2H, d), 7.21 (1H, d), 7.37 (1H, dd), 7.43-7. 45 (4H, m); LRMS ESI m/z 298 [M-H]-

The synthetic route of 263351-43-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/92840; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 156150-67-3, The chemical industry reduces the impact on the environment during synthesis 156150-67-3, name is 2-Chloro-1-fluoro-4-iodobenzene, I believe this compound will play a more active role in future production and life.

General procedure: DG1-tetheredalcohol substrate (0.1 mmol), aryl iodide (0.3 mmol), palladium acetate(0.01 mmol), 3-nitro-5-chloro-pyridone (0.04 mmol) and silver trifluoroacetate(0.25 mmol) were added to a 10 ml reaction vial with a magnetic stir bar, themixture was dissolved with 1 ml of HFIP and then the vial was capped. Thereaction mixture was stirred at 100 C for 20 h. The mixture was cooled toroom temperature, diluted with 2 ml of ethyl acetate and filtered through a padof Celite, and then washed with another 2 ml of ethyl acetate. The filtrate wasconcentrated and redissolved with 5 ml of methanol, cooled with an ice bath,and then sulfonyl chloride (0.2 ml) was added slowly. The resulting mixture wasstirred at room temperature for 30 min and then concentrated, the residue waspurified by preparative thin-layer chromatography to get the arylation product.Full experimental details and characterization of compounds are given inthe Supplementary Information.

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, 2-Chloro-1-fluoro-4-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xia, Guoqin; Weng, Jiang; Liu, Luoyan; Verma, Pritha; Li, Ziqi; Yu, Jin-Quan; Nature Chemistry; vol. 11; 6; (2019); p. 571 – 577;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 101335-11-9, 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. 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of (Z)-4-(l-(l-(tetrahydro-2H-pyran-2-yl)-lH-indazol-5-yl)-2-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)but-l-en-l-yl)benzaldehyde IV, 1.2 equivalents of 2- chloro-4-fluoro-l-iodobenzene, 1.0 mol% palladium acetate (CAS Reg. No. 003375-31-3) and 2.7 mol% triphenylphosphine (CAS 000603-35-0) in THF is added 5.0 equivalents of 15 %-w/w aqueous NaOH at 67 C. The reaction mixture stirred at 67 C for 8 – 12 h. Upon desired conversion, the phases were allowed to settle and the aqueous layer was separated. The organic phase was diluted with toluene and washed with 5% aqueous NaOH followed by water. The organic phase so obtained was concentrated at atmospheric pressure to a desired volume, and then cooled to ambient temperature to give toluene solution (E)-4-(2-(2-chloro- 4-fluorophenyl)-l-(l-(tetrahydro-2H-pyran-2-yl)-lH-indazol-5-yl)but-l-en-l- yl)benzaldehyde III. 1H NMR (300 MHz, DMSO-d6): delta 9.82 (s, 1H), 8.15 (s, 1H), 7.78-7.71 (m, 2H), 7.61 (d, 2H), 7.43-7.27 (m, 3H), 7.15 (m, 3H), 5.86 (dd, 1H), 3.93-3.85 (m, 1H), 3.79-3.68 (m, 1H), 2.44-2.36 (m, 3H), 2.10-1.96 (m, 2H), 1.81-1.67 (m, 1H), 1.63-1.53 (m, 2H), 0.92 (t, 3H); LCMS: 405 [(M-THP+H)+H]+.

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-4-fluoro-1-iodobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BACHMANN, Stephan; FANTASIA, Serena Maria; GOSSELIN, Francis; HAN, Chong; HILDBRAND, Stefan; HUMPHRIES, Theresa; JENNY, Christian; LIM, Ngiap-Kie; MCCLORY, Andrew; MOESSNER, Christian; REGE, Pankaj D.; SAVAGE, Scott; ZHANG, Haiming; (66 pag.)WO2017/60326; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 77317-55-6,Some common heterocyclic compound, 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, molecular formula is C8H8INO2, 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 4-fluorobenzyl zinc chloride (0.5M solution in THF, 27.ImL, 13.55mmol) was added PdCl2(dppf)CH2Cl2 (221mg, 0.27mmoL) and the solution was stirred for 5 minutes. To the solution was added 5-iodoanthranilic acid methyl ester (1.5g, 5.4mmol) and the solution was heated to 70 0C for 1 hour. Allowed to cool, quenched with saturated NH4CI, followed by saturated aqueous Na2EDTA, the solution was extracted with CH2CI2, dried (MgSO4), filtered, and concentrated to yield compound 102 A (1.4g, 100%)

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

Reference:
Patent; SCHERING CORPORATION; WO2009/143049; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 25245-29-8, These common heterocyclic compound, 25245-29-8, name is 5-Iodo-1,2,3-trimethoxybenzene, 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.

PREPARATION EXAMPLE 49 Synthesis of 2,6-Dimethoxy-4-iodophenol To a solution of 5-iodo-1,2,3-trimethoxybenzene (3.2 g) in 1,2-dichloroethane (40 mL) was added aluminum chloride (1.6 g). The mixture was stirred at 60 C. for 4 hours and evaporated. The residue was dissolved in 1 M aqueous sodium hydroxide solution and washed with ether. The aqueous layer was then acidified and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated to give the title compound as white crystalline powder. Yield: 1.0 g (31%)

The synthetic route of 25245-29-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kowa Co., Ltd.; US6498169; (2002); B1;; ; Patent; Kowa Co., Ltd.; US6605620; (2003); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 146137-72-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 146137-72-6, name is 2-Fluoro-6-iodobenzaldehyde belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-FLUORO-6-IODO-BENZALDEHYDE (3.0 g, 12 MMOL), 1, 3-PROPANEDIOL (1. 3 ml, 18 MMOL), and para-toluenesulfonic acid (342 mg, 1.8 MMOL) is heated at reflux in toluene (60 ml) using a Dean-Stark apparatus for 2 hours. The organic layer is washed with brine and dried over MGS04 and evaporated to afford the desired compound (3.65 g).

The synthetic route of 2-Fluoro-6-iodobenzaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/99206; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 25309-64-2, A common heterocyclic compound, 25309-64-2, name is 1-Ethyl-4-iodobenzene, molecular formula is C8H9I, 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 tube (30 mL) equipped with a magnetic stirring bar was charged with 1 (1.5 mmol), 2 (5.25 mmol), Pd(OAc)2 (10 mol%), L1 (10 mol%), and CsOAc (6.0 mmol) in DMSO (1.5 mL), then the tube was sealed, purged with O2, and the mixture was stirred at 100 C for 16 h. At the end of the reaction, the mixture was partitioned between EtOAc (30mL) and H2O (30 mL). The organic layer was separated, and the aqueous layer was extracted further with EtOAc (3 ¡Á 30 mL). The combined organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. Then, the crude mixture was purified by column chromatography (silica gel; n-hexane/EtOAc) to afford the desired product.

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

Reference:
Review; Zheng, Yi-Lin; Xiao, Li; Xie, Qiong; Shao, Li-Ming; Synthesis; vol. 51; 6; (2019); p. 1455 – 1465;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 52570-33-9, These common heterocyclic compound, 52570-33-9, name is Methyl 3-iodo-2-methylbenzoate, 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.

[0470] To a solution of methyl 3-iodo-2-methylbenzoate (15 g, 54.35 mmol) in N,N-dimethylacetamide (200 mL) at rt was added K4[Fe(CN)6].3H2O (5.74 g, 13.59 mmol) and sodium carbonate (5.76 g, 54.35 mmol), followed by palladium acetate (1.5 g) added. The suspension was evacuated and replaced with nitrogen, then heated to 120C for 10 hrs. The reaction mixture was cooled to rt, filtered, and the filtrate was diluted with water (100 mL), and extracted with EA (200 mL) twice. The combined organic layers were washed with water, brine, dried over sodium sulfate, filtered and concentrated providing the crude product, which was purified by column chromatography on silica-gel elution with petroleum ether:EA (from 50/1 to 30/1) providing methyl 3-cyano-2-methylbenzoate (4.6 g, 48.4% yield) as a white solid. MS (ESI) m/z 175.9 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 8.08 (d, J = 7.6 Hz, 1 H), 7.76 (d, J = 8.0 Hz, 1 H), 7.36 (t, J = 7.6 Hz, 1 H), 3.93 (s, 3 H), 2.80 (s, 3 H).

The synthetic route of 52570-33-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOTHERYX, INC.; CHAN, Kyle, W.H.; FUNG, Leah; SULLIVAN, Robert; ERDMAN, Paul, E.; MERCURIO, Frank; (225 pag.)WO2017/201069; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 5326-39-6,Some common heterocyclic compound, 5326-39-6, name is 1-Iodo-4-methyl-2-nitrobenzene, molecular formula is C7H6INO2, 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.

Synthesis example 1 4,4′-dimethyl-2-nitro-1,1′-biphenyl A flask, covered with aluminium foil, was charged with 5.0 g (19 mmol) 4-iodo-3-nitrotoluene, 4.14 g (19 mmol) 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)toluene, 20 ml toluene and 20 ml 2 M potassium carbonate (aq). The mixture was evacuated and charged with argon for three times, after which 2 mol% Pd(PPh3)4 was added. Evacuation and filling with argon was repeated once and the mixture was stirred for 60 hours at reflux temperature. The mixture was allowed to cool to room temperature, the organic layer was separated, dried (MgSO4), filtered and concentrated. After column chromatography (SiO2, hexane/dichloromethane, 60/40, v/v) 4.3 g of product was obtained. 1H NMR (CDCl3): delta 7.64 (d, J=1.5 Hz, 1H), 7.41 (dd, J=1.5 Hz, J=8 Hz, 1H), 7.32 (d, J=8 Hz, 1H), 7.26-7.19 (m, 4H), 2.47 (s, 3H), 2.40 (s, 3H). 13C NMR (CDCl3): delta 149, 138, 138, 134, 133, 133, 132, 129, 128, 124, 21, 21.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Iodo-4-methyl-2-nitrobenzene, its application will become more common.

Reference:
Patent; Koninklijke Philips Electronics N.V.; EP1838671; (2008); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com