Category: 90347-66-3

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. 90347-66-3, name is Methyl 3-iodo-4-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., name: Methyl 3-iodo-4-methylbenzoate

A suspension of Example 191A (2.32 g, 6.62 mmol), methyl 3-iodo-4-methylbenzoate (1.83 g, 6.62 mmol), cesium fluoride (2.01 g, 13.25 mmol) and [(i-butyl)2PCl]2PdCl2 (PXPd, 108 mg, 0.20 mmol) in AyV-dimethylformamide (33 mL) was warmed at 90C for 18 hours. The mixture was cooled and diluted with ethyl acetate and extracted with water (3x) and saturated sodium chloride solution. The solution was dried ( a2S04), filtered, and stirred with 3-(mercaptopropyl) silica gel for 1 hour. Concentration in vacuo afforded a brown oil, which was chromatographed over a 220 g silica gel cartridge, eluting with 10-60% ethyl acetate in hexanes. The solid obtained was triturated with ether-hexanes and collected by filtration. After drying in a vacuum oven at 50 C for 18 hours, these procedures afforded the title compound (1.43 g, 58%>) as white solid. MS (ESI+) m/z (rel abundance) 373 (100, M+H)+, 374 (23).

According to the analysis of related databases, 90347-66-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT GMBH & CO.KG; MARING, Clarence J.; PRATT, John K.; CARROLL, William A.; LIU, Dachun; BETEBENNER, David A.; HUTCHINSON, Douglas K.; TUFANO, Michael D.; ROCKWAY, Todd W.; SCHOEN, Uwe; PAHL, Axel; WITTE, Adreas; WO2012/87833; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 90347-66-3, name is Methyl 3-iodo-4-methylbenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 90347-66-3

Unit Operation 1.1: 1 Sonogashira Reaction AP24595, palladium tetrakis triphenylphosphine (Pd(PPh3)4) , copper (I) iodide (Cul), triethylamine, and tetrahydrofuran (THF) are charged to the reactor. The mixture is stirred and degassed with nitrogen and then pre-degassed AP28141 is charged. The resulting mixture is brought to 45 – 55C and held for not less than 3 hours. The reaction completion is determined by IPC-1 (HPLC). If the IPC-1 criterion is met, the mixture is concentrated to a target volume and cooled. Unit Operation 1.2: Deprotection / 2nd Sonogashira Reaction AP25570, additional palladium tetrakis triphenylphosphine (Pd(PPh3)4), copper (I) iodide (Cul), and tetrahydrofuran (THF) are charged to the reactor. The mixture is concentrated and the water content is determined by IPC-2 (KF). If the IPC-2 criterion is met, the mixture is warmed to 45 – 60C and 25% sodium methoxide solution in methanol is slowly added. The reaction mixture is stirred and held for 30 – 60 minutes at 45 – 55C. The reaction progress is determined by IPC-3 (HPLC). The reaction mixture may be held at a lower temperature during the IPC analysis. If the IPC-3 criterion is met, the process is continued to Unit Operation 1.3. Unit Operation 1.3: Isolation of AP25047 HCI While stirring, the cool reaction mixture is quenched by addition of hydrogen chloride gas. A precipitate forms, and residual hydrogen chloride is removed from the suspension by a nitrogen purge. Tetrahydrofuran (THF) is replaced with toluene by an azeotropic distillation under reduced pressure. The resulting warm slurry is filtered in an agitated filter dryer and the filter cake is triturated and washed with warm toluene. The content of process impurity AP291 16 is determined by IPC-4 (HPLC). If the IPC-4 criterion is met, the wet filter cake is dried with agitation under a flow of nitrogen and reduced pressure at 35 – 45C (jacket temperature). The drying is monitored by IPC-5 (LOD, gravimetric). If the IPC-5 criterion is met, the crude AP25047 HCI is discharged and packaged in FEP bags in a plastic container. The isolated AP25047 HCI can be held for up to 7 days prior to forward processing. Unit Operation 1.4: Work-up The crude AP25047 HCI solid is charged to a reactor with dichloromethane (DCM) and washed with aqueous ammonia. The aqueous phase is back extracted with DCM for yield recovery purposes and the combined organic phase is washed a second time with aqueous ammonia. The organic layer is then washed with aqueous hydrochloric acid until the aqueous phase reaches a pH of 1-2, as indicated by IPC-6 (pH strips). If the IPC-6 criterion is met, the organic phase is treated with aqueous sodium bicarbonate until the aqueous wash reaches a pH of NLT 7, as indicated by IPC-7 (pH strips). The organic phase is briefly concentrated followed by the addition of fresh dichloromethane. The organic solution is passed through a silica gel pad, which is then rinsed with additional fresh dichloromethane for increased product recovery. Unit Operation 1.5: Crystallization of AP25047 The dichloromethane solution is concentrated under reduced pressure, and the dichloromethane is replaced with 2-propanol by azeotropic distillation under reduced pressure to the targeted final volume range. The resulting suspension is then cooled and further aged with agitation. Unit Operation 1.6: Isolation / Drying The precipitated product is isolated in an agitated filter dryer under a flow of nitrogen, and the filter cake is rinsed with 2-propanol. The wet filter cake is dried with agitation under a flow of nitrogen and reduced pressure at 45 – 55C (jacket temperature). The drying is monitored by IPC-8 (LOD, gravimetric). If the IPC-8 criterion is met, the product is sampled and packaged into polyethylene bags and placed within a heat sealed mylar coated aluminum foil bag, within an HDPE shipping container (Expected yield range, 65 – 89%).

The synthetic route of 90347-66-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; MURRAY, Christopher, K.; ROZAMUS, Leonard, W.; CHABER, John, J.; SHARMA, Pradeep; WO2014/93579; (2014); 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. 90347-66-3, name is Methyl 3-iodo-4-methylbenzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H9IO2

Under protective gas A-Ia (0.2 g, 0.724 mmol) together with bis-triphenylphosphine- palladium dichloride (25.4 mg, 0.036 mmol) and copper(I)iodide is added to abs. THF (3 mL) and triethylamine (1 mL). Trimethylsilyl-ethyne is added at RT to this reaction mixture and stirred overnight. For working up it is diluted with EE, poured onto 0.5 M ammonia solution and the aqueous phase is again extracted with EE. The combined organic phases are washed with 0.5 M hydrochloric acid and saturated NaCl solution, extracted again with EE, dried on sodium sulphate, filtered and evaporated down under reduced pressure.The residue is combined with methanolic KOH (1 mL) and stirred for 2 h at RT. The reaction mixture is diluted with EE, poured onto 5 % NaHCO3 solution and extracted twice with EE. The combined organic phases are washed with saturated sodium chloride solution, dried on sodium sulphate, filtered and evaporated down under reduced pressure. Chromatographic purification through a short silica gel frit yields A-2a (HPLC-MS: tRet. = 3.65 min; MS (M+H)+ = 175).

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/3998; (2009); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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);,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 90347-66-3, 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. 90347-66-3, name is Methyl 3-iodo-4-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

A suspension of 4-methylimidazole (1, 3.0 g, 36 mmol), 2 (4.8 g, 20 mmol), K2CO3(4.5 g, 33 mmol), CuI (1.14 g, 6 mmol) and 8-hydroxyquinoline (0.56 g, 4 mmol) in DMSO(20 mL) was heated at 120 C overnight under nitrogen. After cooling, water was added andthe mixture was extracted with EtOAc twice. The combined organic layers were washed withbrine, dried over Na2SO4 and concentrated. The residue was purified by silica gel columnchromatography to give 3 (2.8 g, 58%) as a yellow solid. LCMS (m/z: m+1): 242.2. A mixtureof 4 (7.26 g, 26.3 mmol), 5 (3.0 g, 17.5 mmol), K2CO3 (4.84 g, 35.0 mmol), DMEDA (386 mg,4.38 mmol) and CuI (834 mg, 0.871 mmol) in 90 ml of dioxane was stirred at 100 C under N2for 18h. The mixture was filtered, concentrated and purified by column chromatography to give6 (2.2 g, 39%) as a slightly yellow solid. LCMS (m/z: m+1): 320.2. To a solution of 6 (2.2 g,6.89 mmol) in THF/water (60/30 mL) was added LiOH (496 mg, 20.7 mmol). The reactionwas stirred at room temperature overnight, concentrated. To the residue water (30 ml) wasadded and then acidified to pH 4 with aqueous KHSO4. The precipitate was filtered and washedwith water and EtOAc. The cake was collected and dried to give 7 (1.4 g, 67%) as a whitesolid. LCMS: m/z: (M+1): 306. To a solution of 7 (100 mg, 0.33 mmol) in NMP (2 mL) wasadded SOCl2 (58 mg, 0.49 mmol). The reaction was heated at 90 C for 1 hour before 3 (80mg, 0.33 mmol) was added. The resulting mixture was stirred at 90 C for 3 hours. The reactionwas quenched with water and basified with aqueous NaOH. The mixture was extracted withEtOAc twice. The combined organic layers were washed with brine, dried over Na2SO4 andconcentrated. The residue was purified by reverse prep-HPLC and then silica gel prep-TLC togive 1a (22 mg, 13%) as a white solid.

The chemical industry reduces the impact on the environment during synthesis Methyl 3-iodo-4-methylbenzoate. I believe this compound will play a more active role in future production and life.

Related Products of 90347-66-3, These common heterocyclic compound, 90347-66-3, name is Methyl 3-iodo-4-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.

3-iodo-4-methylbenzoic acid. Methyl-3-Iodo-4-methylbenzoate (3 g, 109 mmol, 1 eq) dissolved in MeOH (30 ml) was added sodium hydroxide (1.3 g, 327 mmol, 3 eq) followed by the addition of water (15 ml). The above solution was stirred at room temperature for 14 h. The solution was concentrated under vacuum, and then added water. The pH of the reaction was bought to 3 using Cone. HCl. The solid obtained was filtered and dried under vacuum, Yield: 2.7 g (96 %). 1HNMR (400MHz, DMSO-d6): delta 2.44 (s, 3H), 7.45 (d, 7- 8.00 Hz ,1H), 7.85 (d, J= 3.18 Hz, IH), 8.31 (s, IH).

Statistics shows that Methyl 3-iodo-4-methylbenzoate is playing an increasingly important role. we look forward to future research findings about 90347-66-3.

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. Application In Synthesis of Methyl 3-iodo-4-methylbenzoate

A mixture of methyl 3-iodo-4-methylbenzoate (1.0 g, 3.6 mmol) and CuCN (389 mg, 4.3 mmol) in NMP (10 mL) is stirred at 200 oC for 1 hour with microwave irradiation.The mixture is diluted with EtOAc / toluene (10:1, 50 mL) to afford precipitate, which is separated by filtration through a pad of Celite. The filtrate is washed with water (30 mL x 3), brine (20 mL x 1), dried over sodium sulfate.The insoluble materials are separated by filtration and the filtrate is concentrated.The residue is purified by column chromatography on silica-gel eluting with n-hexane / EtOAc (7:1 to 6:1) to give 511 g (81% yield) of the title compound as a white solid. 1H-NMR (400 MHz, CDCl 3) delta8.27 (1H, d, J = 1.8 Hz), 8.13 (1H, dd, J = 8.6, 1.8 Hz), 7.42 (1H, d, J = 8.6 Hz), 3.94 (3H, s), 2.61 (3H, s).

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.

Application of 90347-66-3, 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. 90347-66-3 name is Methyl 3-iodo-4-methylbenzoate, 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.

To a solution of 3-IODO-4-METHYL-BENZOIC acid methyl ester (13.50 g, 48.92 MMOL) in THF (260 mL) was added 2 M solution of ISOPROPYLMAGNESIUM chloride in THF (24.5 mL, 49.00 MMOL) AT-50C. After the reaction mixture was stirred at the same temperature for 30 min, compound 440 (13.39 G, 40.70 MMOL) was added. The solution was warmed up to room temperature and stirred at the same temperature for 2 h. The reaction was then quenched with saturated aqueous solution of NH4CI. The aqueous phase was extracted twice with diethyl ether. The combined organic phases were dried over MGS04 and concentrated in vacuo. The crude material was taken up in ethanol and heated for reflux. The obtained solution was cooled down to room temperature. The crystals were filtered off and dried

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

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. 90347-66-3, name is Methyl 3-iodo-4-methylbenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 90347-66-3

Compound 5.4. Methyl 4-methyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)benzoate. A mixture of methyl 3-iodo-4-methylbenzoate (compound 5.3, 5.00 g, 18.1 mmol), 4,4,4′,4′,5,5,5′,5,-octamethyl-2,2′-bi(l ,3,2-dioxaborolane) (5.20 g, 20.5 mmol), KOAc (5.33 g, 54.3 mmol) and PdCl2(dppf CH2Cl2 (0.74 g, 0.91 mmol) in DMSO (50 mL) was degassed with argon. The mixture was then heated at 80 C under argon overnight. The mixture was allowed to cool then partitioned between EtOAc (400 mL) and water (80 mL). The organic phase was washed with water (80 mL), saturated aqueous NaHC03 (80 mL), brine (80 mL), dried (MgS04), filtered, and concentrated under reduced pressure. The residue was purified with silica gel chromatography (hexanes: EtOAc 20: 1) to yield the title compound as a white crystalline solid (3.56 g, 71 %). NMR (400 MHz, CDC13) 5 8.41 (d, J = 1.9 Hz, 1 H), 7.97 (dd, J= 8.0 Hz, 2.0Hz, 1H), 7.23 (d, J= 8.0 Hz, 1H), 3.90 (s, 3H), 2.58

The synthetic route of 90347-66-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; 3-V BIOSCIENCES, INC.; OSLOB, Johan D.; MCDOWELL, Robert S.; JOHNSON, Russell; YANG, Hanbiao; EVANCHIK, Marc; ZAHARIA, Cristiana A.; CAI, Haiying; HU, Lily W.; WO2014/8197; (2014); 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. 90347-66-3, name is Methyl 3-iodo-4-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Methyl 3-iodo-4-methylbenzoate

Compound 27.1. Methyl 3-acetyl-4-methylbenzoate. Into a 250-mL round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a mixture of methyl 3-iodo-4-methylbenzoate (compound 5.3, 4.50 g, 16.3 mmol), 1- (vinyloxy)butane (4.21 mL, 32.6 mmol), TEA (4.53 mL, 32.5 mmol), 1,3- bis(diphenylphosphino)propane (672 mg, 1.63 mmol) and Pd(OAc)2 (349 mg, 1.55 mmol) in DMSO (50 mL). The mixture was stirred for 12 hours at 120 C, then cooled to room temperature. The pH was adjusted to 1-2 with aqueous hydrogen chloride (2 M) and stirred for 1 hour. The aqueous phase was extracted with ethyl acetate (3 x 200 mL) and the combined organic layers were washed with water (100 mL), then brine (3 x 100 mL), dried (Na2S04), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1 :50) as the eluent to yield 1.45 g (46%) of the title compound as a yellow solid.

According to the analysis of related databases, 90347-66-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; 3-V BIOSCIENCES, INC.; HEUER, Timothy Sean; OSLOB, Johan D.; MCDOWELL, Robert S.; JOHNSON, Russell; YANG, Hanbiao; EVANCHIK, Marc; ZAHARIA, Cristiana A.; CAI, Haiying; HU, Lily W.; WO2015/95767; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com