Tag: M.W=200-300

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. 672293-33-3, name is Methyl 4-amino-5-iodo-2-methylbenzoate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 4-amino-5-iodo-2-methylbenzoate

To a solution of methyl 4-amino-5-iodo-2-methylbenzoate 2 (0.84 g, 2.90 mmol, 1 eq.) in DMF (10 mL), 2-oxobutyric acid (1.48 g, 14.5 mmol, 5 eq.) and DABCO (0.975 g, 8.7 mmol, 3 eq.) were added. The solution was stirred for 5 min and then palladium (II) diacetate (0.03 g, 0.145 mmol, 0.05 eq.) was added. The mixture was warmed to 105C, stirred during 16 h and then concentrated. The resulting solid was dissolved in AcOEt (150 mL) and washed with water (150 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuuo to obtain dark brown solid which was purified by trituration in AcOEt to give the desired indole 6 as grey powder (358 mg, 1.45 mmol, 50%); Mp : 280-282C (Dec.); Rf = 0.61 (SiO2, Cyc/AcOEt, 5/5); 1H NMR (400 MHz, CD3OD) 8.30 (s, 1H, H-4), 7.25 (s, 1H, H-7), 3.99 (s, 3H, CH3), 2.65 (s, 3H, CH3), 2.59 (s, 3H, CH3); 13C NMR (100 MHz, CD3OD) 168.1 (C=O), 165.3 (C=O), 139.6 (C), 137.2 (C), 128.0 (C), 127.7 (C), 125.6 (CH), 122.3 (C), 118.9 (C), 114.8 (CH), 52.1 (CH3), 22.9 (CH3), 9.94 (CH3); HR-ESIMS: [M-H]- m/z calcd for C13H12NO4 246.0766 found 246.0777.

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; Vogrig, Alexandre; Boucherle, Benjamin; Deokar, Hemantkumar; Thomas, Isabelle; Ripoche, Isabelle; Lian, Lu-Yun; Ducki, Sylvie; Bioorganic and Medicinal Chemistry Letters; vol. 21; 11; (2011); p. 3349 – 3353;,
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Some common heterocyclic compound, 90347-66-3, name is Methyl 3-iodo-4-methylbenzoate, molecular formula is C9H9IO2, 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. Safety of Methyl 3-iodo-4-methylbenzoate

A mixture of 19 (1366 mg, 4.63 mmol), (S)-tert-butyl piperidin-3-ylcarbamate (1020mg, 4.63 mmol) and K2CO3 (768 mg, 5.56 mmol) in DMF (8 mL) was stirred at roomtemperature overnight. Water was added and the mixture was extracted with EtOAc twice. Thecombined organic layers were washed with brine, dried over Na2SO4 and concentrated. Theresidue was purified by silica gel column chromatography to give 34 (870 mg, 45%) as aslightly yellow solid. LCMS (m/z: m+1): 414.0, 116.1. A suspension of 34 (870 mg, 2.1 mmol),1 (517 mg, 6.3 mmol), K2CO3 (580 mg, 4.2 mmol), CuI (120 mg, 0.63 mmol) and 8-hydroxyquinoline (61 mg, 0.42 mmol) in DMSO (8 mL) was heated at 120C overnight undernitrogen. After cooling, water was added and the mixture was extracted with EtOAc twice. Thecombined organic layers were washed with brine, dried over Na2SO4 and concentrated. Theresidue was purified by silica gel column chromatography to give 35 (630 mg, 72%) as aslightly yellow solid. LCMS (m/z: m+1): 416.3. A mixture of 35 (630 mg, 1.52 mmol) andSnCl2 2H2O (1369 mg, 6.06 mmol) in EtOH (13 ml) was heated at 80C for 1 h. After cooling,silica gel was added to the reaction and the mixture was concentrated to dryness. The residuewas purified by silica gel column chromatography to give 36 (430 mg, 74%) as a slightlyyellow solid. LCMS (m/z: m+1): 386.4. A mixture of 37 (9.5 g, 73.3 mmol), 4-fluorophenylboronic acid (10.3 g, 73.3 mmol), Na2CO3 (15.5 g, 147 mmol), and Pd(PPh3)4 (1.5g) in CH3CN/H2O (2/1, 200 mL) was heated at reflux under N2 for 16 h. After cooling, themixture was diluted with water and extracted with EtOAc twice. The combined organic layerswere washed with brine, dried over Na2SO4, filtered, concentrated and purified by silica gelcolumn chromatography to give 38 (5.1 g, 37%) as a slightly yellow solid. LCMS (m/z: m+1):190.2. A mixture of 38 (5.1 g, 27.0 mmol), 39 (11.2 g, 40.4 mmol), K2CO3 (7.5 g, 54.0 mmol),DMEDA (476 mg, 5.4 mmol) and CuI (1.28 g, 6.7 mmol) in 100 mL of dioxane was stirred at100C under N2 for 24 h. The mixture was filtered, concentrated and purified by columnchromatography to give 40 (1.6 g, 18%) as a slightly yellow solid. LCMS (m/z: m+1): 338.3.To a solution of 40 (1.6 g, 4.74 mmol) in THF/H2O (32/16 mL) was added LiOH (341 mg,14.2 mmol). The reaction was stirred at room temperature overnight and then concentrated. Tothe residue, water was added and then acidified to pH 4 with aqueous KHSO4. The precipitatewas filtered and washed with water and EtOAc. The cake was collected and dried to give 41(1.3 g, 85%) as an off-white solid. LCMS (m/z: m+1): 324.1. A mixture of 36 (130 mg, 0.34mmol), 41 (109 mg, 0.34 mmol), HATU (257 mg, 0.68 mmol) and DIEA (218 mg, 1.69 mmol)in DMF (2 mL) was heated at 70C overnight. After cooling, the reaction mixture was directlypurified by reverse prep-HPLC and then silica gel prep-TLC to give 42 (33 mg, 14%) as aslightly yellow solid. LCMS (m/z: m+1): 691.3. To a solution of 42 (33 mg, 0.048 mmol) inCH2Cl2 (2 mL) was added TFA (1 mL) and the reaction was stirred at room temperature for 4h before being concentrated under reduced pressure. The residue was treated with water,basified with 0.5 N NaOH and extracted with CH2Cl2/MeOH (15/1) 3 times. The combinedorganic layers were dried over Na2SO4, filtered, concentrated and purified by reverse prep-HPLC to give 2a (14 mg, 50%) as an off-white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 90347-66-3, its application will become more common.

Reference:
Article; Bonnar, James; Dixon, Ian; Evison, Benny J.; Kelly, Graham E.; Kumar, Sanjay; Lambert, Gilles; Nativel, Brice; Palmer, James T.; Parmar, Jasneet; Rathi, Anuj Kumar; Suchowerska, Alexandra K.; Tang, Wei; Teng, Yanfen; Treutlein, Herbert; Wang, Jie; Xu, Yanfeng; Zeng, Jun; Zhu, Qing; Chemello, Kevin; Bioorganic and medicinal chemistry; vol. 28; 6; (2020);,
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These common heterocyclic compound, 6937-34-4, name is 3-Iodophthalic acid, 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. category: iodides-buliding-blocks

[0030] The synthesis of mIBX is readily accomplished from commercially available 3-nitrophtalic acid as follows: esterification of 3-nitrophtalic acid via the corresponding acid chloride to give nitrodiester (100%), which upon catalytic hydrogenation provides the aminodiester (100%). Diazotization is then performed, followed by iodination of the aminodiester to provide dimethyl 3-iodophthalate in about 91 % yield. This is followed by saponification, then acidification of dimethyl 3-iodophthalate to give 3-iodophthalic acid in about 93 % yield. 3-iodophthalic acid is then oxidized to form the water-soluble MIBX. This process is carried out using KBrO3 in 0.73H2SO4 at 55-60 C. as follows: KBrO3 (5 g, 30 mmol) is added in portions to a suspension of 3-iodophthalic acid (5 g, 17.1 mmol) in 70 ML of 0.73 M H2SO4 over a period of 20 minutes; The mixture is then maintained at 55-60 C. for 12 hours and the resulting clear orange solution is evaporated to yield an off-white solid, which is triturated with 30 ML of water at 0 C. for 2 hours and filtered to obtain a white solid.This is further triturated with hexane (100 ML) for 6 hours and filtered to give MIBX (3.9 g, 71%) as a white solid with a melting point of 258-260 C. The approximately 70% yield for the conversion of 3-iodophthalic acid to MIBX is the isolated yield of MIBX, with the actual conversion near quantitative as evident from monitoring the oxidation of 3-iodophthalic acid to MIBX by 1H NMR spectroscopy. Water-soluble MIBX is isolated as an analytically pure white solid.The synthesis of MIBX from 3-nitrophthalic acid is illustrated in . The physical properties of MIBX are as follows: mp 258-260 C.; IR (KBr), 3503 3469, 3050, 1708, 1631, 1588, 1369, 730, 700 cm-1; 1H NMR (D2O), 300 MHz): delta 8.35 (dd, J=7.9, 1.0 Hz, 1H), 8.09 (t, J=7.9 Hz, 1H), 7.94 (dd, J=7.9, 1.0 Hz, 1H); 13C NMR (D2O, 75 MHz): delta 125.5, 127.5, 132.5, 134.7, 137.0, 147.1 (ring carbons), 168.9, 172.9 (carbonyl carbons).

The synthetic route of 3-Iodophthalic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Vinod, Thottumkara K.; Thottumkara, Arun P.; US2004/30187; (2004); A1;,
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Related Products of 618-91-7, 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. 618-91-7, name is Methyl 3-iodobenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Cu [(I)] iodide (10 mg, 0.05 mmol), potassium carbonate (276 mg, 2.0 mmol) and Methyl 3-iodobenzoate (276 mg, 1.0 mmol) were charged into a screw-capped test tube with Teflon-lining. The tube was evacuated and backfilled with argon (3 cycles). Anhydrous DME (1.0 mL) and 3-methoxythiophenol (124 muL, 1.0 mmol) were added by syringes at room temperature. The tube was heated to [80 C] and stirred for 22 hours. The reaction mixture was then allowed to reach room temperature. Ethyl acetate (approx. 5 mL) and dodecane (227 [AL,] GC standard) were added. The aliquot was analyzed GC. The reaction mixture was then filtered and concentrated. The crude product was purified by column chromatography on silica gel using hexane/ethyl acetate = 20/1 to afford colorless liquid as the titled product (220 mg, 81% yield). Rf= 0.5 (hexane/ethyl acetate = [10/1). IN] NMR [(CDC13,] 300 MHz) 8 8.02-8. 03 (m, [1] H), 7.89 (dt, 1 H, J=1. 2 Hz, 8.1 Hz), 7.45-7. 49 (m, 1 H), 7.34 (t, 1 H, [J=] 7.5 Hz), 7.21 (t, 1 H, [J=] 8.1 Hz), 6.86-6. 92 (m, 2 H), 6.79 (ddd, [1] H, J = 0. 6 Hz, 2.4 Hz, 8.1 Hz), 4.34 (q, 2 H, J= 7. 2 Hz), 3.76 (s, 3 H), 1.37 (t, 3 H, J = 7.2 Hz). 13C NMR (CDC13, 75 MHz) 8 166.0, 160.2, 136.5, 136.3, 135.2, 132.0, 131.7, 130.3, 129.3, 128. 4,123. 7,116. 6,113. 5,61. 5,55. 7,14. 7. IR (neat, [CM~L)] 3064,2981, 2960,2937, 2360,2342, 1717. MS (EI) m/z (relative intensity) [288] (100), 243 (30). Anal. Cald. for [C16H1603S,] Cald. C: 66.64, H: 5.59 ; Found C: 66.87, H: 5.66.

The synthetic route of Methyl 3-iodobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; WO2004/13094; (2004); A2;,
Iodide – Wikipedia,
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Synthetic Route of 13421-00-6,Some common heterocyclic compound, 13421-00-6, name is 5-Chloro-2-iodobenzoic acid, molecular formula is C7H4ClIO2, 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 S-chloro-2-iodobenzoic acid (3.0 g,10.62 mmol), 50C12 (12 mE) and DMF (0.6 mE) was gently warmed with a heat gun until the mixture became homogeneous (15 mm). The solution was maintained at 23 C. for additional 30 mm and then the solution was concentrated. MeOH (24 mE) was added to the crude residue and the solution was maintained at 23 C. for 30 mm. The solution was concentrated and the residue was purified by flash chromatography on l3iotage silica gel cartridge (cyclohexane to cyclohexane_EtOAc=85: 15) to afford methyl S-chloro-2-io- dobenzoate (3.02 g, 10.20 mmol, 96%).

The synthetic route of 13421-00-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIESI FARMACEUTICI S.p.A.; Biagetti, Matteo; Capelli, Anna Maria; Accetta, Alessandro; Carzaniga, Laura; US2015/166549; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 75581-11-2,Some common heterocyclic compound, 75581-11-2, name is 4-Iodo-1-methoxy-2-methylbenzene, molecular formula is C8H9IO, 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 mixture of 1,4-dioxa-spiro[4,5]dec-7-en-8-boronic acid pinacol ester (25.0 g, 93.9 mmol), 4-iodo-2-methylanisole (28.0 g, 113 mmol), 1,1?-bis(diphenylphosphino)ferrocenedichlorlopalladium(II) (1.38 g, 1.89 mmol), dioxane (470 mL) and 1MNa2CO3 (282 mL, 282 mmol) was degassed with 3 vacuum/N2 cycles, stirred at 50 C for 2.5 h, and then allowed to cool to a The mixture was diluted with ethyl acetate (500 mL) and washed with saturated NaHCO3 (500 mL x 2). The aqueous layers were back extracted with ethyl acetate (200 mL). The combined ethyl acetate extracts were dried (Na2SO4), filtered, concentrated and purified by silica gel chromatography (0-5% ethyl acetate in hexanes) to give 8-(4-methoxy-3-methylphenyl)-1,4- dioxaspiro[4.5]dec-7-ene (19.9 g, 81%). ?H NMR (400 MHz, DMSO-d6): 7.21-7.16 (m, 2H), 6.85 (d, 1H), 5.89-5.84 (m, 1H), 3.90 (s, 4H), 3.76 (s, 3H), 2.52-2.47 (m, 2H), 2.32 (br s, 2H),2.13 (s, 3H), 1.77 (t, 2H); MS: 261.1 [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 4-Iodo-1-methoxy-2-methylbenzene, its application will become more common.

Reference:
Patent; METACRINE, INC.; SMITH, Nicholas D.; GOVEK, Steven P.; (192 pag.)WO2017/49177; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 128140-82-9,Some common heterocyclic compound, 128140-82-9, name is 1-(Difluoromethoxy)-4-iodobenzene, molecular formula is C7H5F2IO, 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 degassed mixture of 5-methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxymethyl]-furan-2-carboxylic acid methyl ester (119) (200mg, 0.54mmoles), 4-difluoromethoxy-1-iodo-benzene (175mg, 0.65mmoles), 2M aqueous cesium carbonate (0.81ml) and), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1 : 1) (20mg) in 1,4-dioxan (10ml), under an argon atmosphere was heated at 80C for 20h. Further quantities of 4-difluoromethoxy-1-iodo-benzene (87.5mg, 0.0.27mmoles) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1 : 1) (10mg) were added and heating at 80C was continued for 4 hours. After cooling, the mixture was concentrated. The residue was dissolved in dichloromethane and washed with water and brine, and dried. The solvent was evaporated and the residue was purified by flash chromatography using petrol (40-60)/diethyl ether 9 : 1v/v as eluent to afford compound 128 (120mg) as a wax. LC/MS System A ; Rt = 4.14 mins.

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

Reference:
Patent; PHARMAGENE LABORATORIES LIMITED; WO2004/67524; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 54413-93-3, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 54413-93-3 as follows.

2~lodo-5-methoxybeiizoie acid (1.74 g, 6.25 mmol), /V-(3-dimethylaminopropyl)-AT- ethylcarbodiimide hydrochloride (1.44 g, 7.5 mmol), l-hydroxybenzotriazole (676 mg, 5.0 mmol), Ar, V-diisopropy]ethylamine (2.61 mL, 15.0 mmol), and benzylamine (546 pL, 5.0 mmol) were dissolved m anhydrous DMF (12.5 mi.) and stirred at room temperature for 16 hours. The reactin mixture was diluted with an excess of EtOAc and washed five times with water and brine. The organic layer was dried over Na2S04, filtered and concentrated. The residue was purified by flash column chromatography (EtOAc : DCM = 0; 100 to 30:70) to give V-benzyl-2-iodo-5-methoxybenzamide (1.534 g, 84%) as a white solid.

According to the analysis of related databases, 54413-93-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael S.; DE CLERCQ, Dries; JANG, Jaebong; JANNE, Pasi; TO, Ciric; ECK, Michael; PARK, Eunyoung; HEPPNER, David; (0 pag.)WO2019/164953; (2019); A1;,
Iodide – Wikipedia,
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Related Products of 460-37-7, These common heterocyclic compound, 460-37-7, name is 1,1,1-Trifluoro-3-iodopropane, 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.

To a solution of Zinc ((1 S,3S)-3-(methyl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4- yl)amino)cyclobutyl)-methanesulfinate (100 mg, 0.230 mmol) in DMSO (8 mL) was added 1 ,1 ,1 – trifluoro-3-iodopropane (1 29 mg, 0.575 mmol) and K2CO3(95.4 mg, 0.690 mmol). The solution was stirred at 50oC for 2 hours by which time LCMS showed the reaction was complete. The mixture was diluted with water (30 mL), extracted with EtOAc (30 mL x 2). The combined organ- ic layer was washed with brine (50 mL), dried over Na2SO4, filtered and concentrated. The crude product was purified by silica gel chromatography (EtOAc: PE=2:1 ) to afford the title compound (45 mg, 37%) as a colorless oil. LCMS m/z 531 .1 [M+H]+

Statistics shows that 1,1,1-Trifluoro-3-iodopropane is playing an increasingly important role. we look forward to future research findings about 460-37-7.

Reference:
Patent; PFIZER INC.; COFFMAN, Karen J.; DUERR, James M.; KAILA, Neelu; PARIKH, Mihir D.; REESE, Matthew R.; SAMAD, Tarek; SCIABOLA, Simone; TUTTLE, Jamison B.; VAZQUEZ, Michael L.; VERHOEST, Patrick Robert; (254 pag.)WO2016/24185; (2016); A1;,
Iodide – Wikipedia,
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Application of 19718-49-1, 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. 19718-49-1, name is Methyl 4-amino-3-iodobenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of 25 g 4-Amino-3-iodo-benzoic acid methyl ester, 19 ml 2-Oxo-propionic acid, 30.4 g 1,4-Diaza-bicyclo[2.2.2]octane and 1 g Pd(OAc)2 in 200 ml DMF was heated under argon to 100C. After 5 h the reaction mixture was concentrated under reduced pressure and the residue was partitioned between 300 ml ethyl acetate and 200 ml 1 M hydrochloric acid. The organic layer was dried over MgSO4 and the solvent removed under reduced pressure to yield a yellow solid (6.4 g). From the aqueous layer additional product slowly precipitated as a white solid (7.9 g) which was collected by filtration. Both fractions were combined, dried in vacuo and used in the next reaction without further purification. Yield: 14.3 g MS (ES+): m/e =220.

The synthetic route of Methyl 4-amino-3-iodobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Aventis Pharma Deutschland GmbH; EP1479677; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com