Tag: M.W=300-400

Reference of 869365-97-9, These common heterocyclic compound, 869365-97-9, name is (5-Chloro-2-iodophenyl)(2,6-difluorophenyl)methanone, 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.

(5-chloro-2-iodophenyl)(2-fluoro-6-methoxyphenyl)methanone (3)[0148] Into a reactor at room temperature was added 2 (67.6kg, 179mol) and MTBE (344L). The mixture was warmed to 40 C and stirred for 30rnin until solids fully dissolved. The mixture was then cooled to 25 to 30 C. Sodium methoxide as a 25% w/w solution in methanol (45.2kg, 209mol) was added over a minimum of 90min at 25 to 30 C. The reaction mixture was stirred for at least 2h until >99.0% conversion was obtained by HPLC analysis. Water (483L) was added slowly over 30min while maintaining the temperature between 20 and 25 C. The layers were separated and the aqueous phase was extracted with MTBE (77L). The combined organic extracts were washed with a dilute brine solution (38kg NaCl in 342L water). The organic layer was filtered, washed with water (242L) and the organic phase was filtered. The resulting organic phase was concentrated until 360L of solvent were removed while maintaining the internal temperature below 70 C. Isobutanol (302L) was added and the mixture was concentrated while maintaining the internal temperature below 70 C until 307L of solvent were removed. A second portion of isobutanol (330L) was added and the mixture was concentrated while maintaining the internal temperature below 70 C until 210L of solvent were removed. The mixture was heated to 60 to 85 C until a clear solution was obtained and cooled to 50 C. A slurry of seed crystals (50g in 150mL isobutanol) was added and the mixture was cooled to 40 C. A second slurry of seed crystals (30g in 60mL isobutanol) was added and the mixture was cooled to 20 to 25 C over a minimum of 3h. The resulting mixture was stirred an additional 2h. The mixture was filtered and washed with isobutanol (2 x 65L). The resulting wet cake was dried at 20 to 35 C under vacuum to provide 50.9kg of crude 3. Into a separate reactor was charged crude 3 and isobutanol (69L). The mixture was heated to 75 to 80 C until a clear solution was obtained. The reaction mixture was cooled to 55 C and a slurry of seed crystals (50g in 500mL isobutanol) was added. The mixture was stirred for 30rnin at 55 C, cooled to 20 to 25 C over a minimum of 3h and stirred an additional 2h. The mixture was filtered and washed with isobutanol (2 x 31L). The wet cake was dried under vacuum at 40 C to provide 46.0kg (66% yield) of purified 3. ? NMR (300 MHz, CDCL) delta 7.88 (d, J=8.2 Hz, 1H), 7.42 (m, 2H), 7.13 (dd, J=2.3, 8.2 Hz), 6.76 (m, 2H), 3.73 (s, 3H); MS (ESI) m/z 391.2 (M + H+, 30%).

Statistics shows that (5-Chloro-2-iodophenyl)(2,6-difluorophenyl)methanone is playing an increasingly important role. we look forward to future research findings about 869365-97-9.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; ARMITAGE, Ian; COOPER, Martin, I.; EDDLESTON, Mark, D.; FAIBER, Neil, C.; MCCUBBIN, Quentin, J.; WATT, Stephen, W.; WO2011/103089; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 180624-08-2, 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. 180624-08-2, name is 4-Bromo-2-iodo-6-nitroaniline belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

3-Bromo-5-iodonitrobenzene.4-bromo-2-iodo-6-nitroaniline (5 g, 0.0145 mol) was added in portions to stirred concentrated sulfuric acid (60 ml) keeping the temperature at 0-50C. After stirring in the cold for 1 h, sodium nitrite (2.3 g, 0.0326 mol) was added and the reaction mixture stirred in the cold for a further 2 h. The reaction mixture was then poured into ice (250 ml). The resultant mixture was added, in portions, to a boiling solution of copper (II) sulfate (0.36 g, 0.00145 mol) in ethanol (150 ml) and boiled for a further 2 h. The reaction mixture was cooled to ambient temperature and extracted with ethyl acetate (300 ml) which was washed with saturated sodium hydrogen carbonate solution (250 ml) and dried (MgSO4). The solvent was removed in vacuo to give 3- Bromo-5-iodonitrobenzene as a yellow solid (4.21 g, 88 %) which was used without further purification. 1H NMR (400MHz,delta,CDCI3): 8.18(1 H,s), 8.34(1 H,s), 8.50(1 H,s)

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-Bromo-2-iodo-6-nitroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PROLYSIS LTD.; WO2007/148093; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 1252046-13-1, name is 2-Bromo-5-iodobenzonitrile, molecular formula is C7H3BrIN, 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. SDS of cas: 1252046-13-1

Under nitrogen condition, the compound B was dissolved in dioxane, and the compound A (0.9 equivalent) was added. Potassium phosphate (4.0 equivalent) was added, and Cut (0.2 equivalent) and 1,2-diaminocyclohexane (0.2 equivalent) were added. The mixture was refluxed and stirred for 12 hrs, and then the reaction was finished. The resultant was extracted using an organic solvent, and the organic solvent was removed. The resultant was columned and reprecipitated such that the compound C was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1252046-13-1, its application will become more common.

Adding a certain compound to certain chemical reactions, such as: 1189352-83-7, name is 3-Chloro-5-iodobenzotrifluoride, 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 1189352-83-7, Quality Control of 3-Chloro-5-iodobenzotrifluoride

A mixture of 1-chloro-3-iodo-5-(trifluoromethyl)benzene (150 g, 489 mmol), (R)- ethyl 5-oxopyrrolidine-2-carboxylate (108 g, 683 mmol), copper (I) iodide (23.3 g, 122 mmol), CsCO3 in 1,4-dioxane (1 L) was stirred under an atmosphere of nitrogen followed by the addition of N,N’-diemthyl-1,2-ethanediamine (26 mL, 245 mmol). The mixture was heated to 40 C for 4 hours, followed by the addition of copper (I) iodide (11.4 g, 60 mmol) and N,N’-diemthyl-1,2- ethanediamine (13 mL, 123 mmol) and heating at 40 C was continued overnight. The was diluted with water (600 mL) and saturated aqueous NH3 and MTBE (600 mL) and the mixture was stirred for 10 min and allowed to separate into two distinct layers. The aqueous layer was separated and extracted with MBTE (2 x 300 mL) and the combined organic layers were washed sequentially with a mixture of water (150 mL)/ saturated brine (15 mL), followed by 2 N HCl (300 mL) and then water (230 mL). The organic phase was dried over Na2SO4, filtered and concentrated in vacuo to afford 10 as an oil. 1H NMR (400 MHz, CHLOROFORM-d) delta: 7.85 (t, J= 2.13 Hz, 1H), 7.63 (t, J= 2.01 Hz, 1H), 7.41 (t, J= 1.88 Hz, 1H), 4.73 (dd, J= 2.89, 8.91 Hz, 1H), 4.18 – 4.29 (m, 2H), 2.73 – 2.83 (m, 1H), 2.57 – 2.65 (m, 1H), 2.49 – 2.55 (m, 1H), 2.19 – 2.31 (m, 1H), 1.68 (s, 1H), 1.22 – 1.32 (m, 3H). MS: 335; MS Found: 335.9([M+1]+.

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

Synthetic Route of 180624-10-6, 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. 180624-10-6, name is Methyl 4-amino-3-iodo-5-methoxybenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 94-1 (7.1 g, 23 mmol) in DCM (10 mL) was added BBr3 (3 mL) at 0 C. The mixture was stirred at 0 C. for 30 mins, and the reaction was quenched with aq. NaHCO3 (150 mL) and extracted with EA (300 mL). The organic layer was washed with brine (50 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography using 3080% EA in PE as eluent to give 94-2 (4.8 g, 71.3%) as a yellow oil. MS: m/z 293.8 [M+H]+.

The synthetic route of Methyl 4-amino-3-iodo-5-methoxybenzoate has been constantly updated, and we look forward to future research findings.

Synthetic Route of 13101-40-1, A common heterocyclic compound, 13101-40-1, name is 1-Bromo-3-chloro-5-iodobenzene, molecular formula is C6H3BrClI, 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 100 mL two-necked flask was dried in the oven and charged with 1-bromo-3-chloro-5-iodobenzene (2.02 g, 6.37 mmol) and NiCl2(PPh3)2 (0.208 g, 0.318 mmol). The reaction mixture was vacuum and back-filled with nitrogen. Diethyl ether (20 ml) and (2,4,6-triisopropylphenyl)magnesium bromide in THF (12.73 ml, 6.37 mmol) was added and heated at 55 C. for 18 hrs. The reaction mixture was then cooled down and coated on celite and chromatographed on silica (Heptane) (1.74 g, 69%).

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.

Synthetic Route of 136618-42-3,Some common heterocyclic compound, 136618-42-3, name is Benzyl 4-iodobenzoate, molecular formula is C14H11IO2, 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 4-iodobenzoic acid benzyl ester (12.61 g, 37.3mmol) in dry dioxane (20ml) was added 6-methyl-1 H-indazol-4-amine (5.48g, 37.3mmol), copper (I) iodide (71 mg, 0.37mmol), diaminocyclohexane (0.42g, 3.73mmol) and potassium phosphate (16.6g, 78.3mmol) washed in by more dry dioxane (30ml). The mixture was heated under reflux for 3.25hr. The mixture was allowed to cool gradually to RT. The mixture was partitioned between water and ethyl acetate and the aqueous phase was extracted with more ethyl acetate. The combined organics were washed with brine, dried and evaporated. This gave a brown solid, 13.58g. This was combined with 0.66g of crude material from a previous batch. The combined material was columned on 7734 silica (500ml) eluting with 10% ethyl acetate in DCM, then 20% ethyl acetate to give a brown/yellow solid, 5.12g. The material was dissolved in the minimum quantity of ethyl acetate at 6O0C (40ml). Then warm cyclohexane (70ml) was added and this gradually gave a precipitate which was then cooled in an ice bath and the solid was collected by vacuum filtration and washed with cyclohexane/ethyl acetate (4:1 , 40ml) to give the title compound as a beige solid (4.29g, 32%). LCMS; tRET = 3.77min, 98% ES +ve 358. 1H NMR (400 MHz, CHLOROFORM-d) deltappm 8.25 (d, 2H) 8.1 1 (s, 1 H) 7.85 (d, 2H)7.49 (d, 2H) 7.35 – 7.45 (m, 3H) 7.01 (s, 1 H) 6.32 (s, 1 H) 5.42 (s, 2H) 4.15 (s, 2H) 2.42 (s, 3H).The filtrate was evaporated (0.96g) and added to a mixed fraction (yellow solid, 6.81 g). The purification procedure was repeated with this combined material; dissolved in ethyl acetate (ca. 55ml), then cyclohexane was added (100ml) to give a pale yellow solid; 5.49g. This material still contained impurity and so it was combined with the concentrated filtrate (1.88g). The purification procedure was repeated once more with ethyl acetate (70ml) and less cyclohexane (60ml) to give the title compound as a pale cream solid, (2.84g, 21 %).1H NMR (400 MHz, CHLOROFORM-d) deltappm 8.24 (d, 2H) 8.09 (s, 1 ) 7.85 (d, 2H) 7.49 (d, 2H) 7.35 – 7.45 (m, 3H) 7.01 (s, 1 H) 6.32 (s, 1 H) 5.42 (s, 2H) 4.15 (s, 2H) 2.41 (s, 3H).

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

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. 136618-42-3, name is Benzyl 4-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 136618-42-3

General procedure: To a DMF solution (10 mL) of benzyl iodobenzoate (100 mg, 4 mmol), tetrabutylammonium chloride (1.7 g), NaHCO3(0.9 g, 11 mmol) and palladium acetate (80 mg) at 0C, a solution of allyl alcohol (0.41 mL, 6 mmol) in DMF (2 mL) was added. The reaction mixture wasallowed to warm slowly to room temperature, heated at 50Cfor 2 h, diluted with 3N HCl (50 mL), and extracted with EtOAc (5 × 15 mL).The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The product containing1h-1or1r-1was used as such for the next reaction.To a solution of (2-carboxyethyl) triphenylphosphonium bromide (4 mmol) in THF (30 mL), a solution of 2 M lithium bis(trimethylsilyl)amide (LHMDS) (10 mmol, 5 mL THF) was slowly added under nitrogen atmosphere at -78C. The reaction mixture was stirred at -78C for 15 mins, and allowed to warm slowly to 0C for 0.5 h. After being stirred at 0C for 1 h, a solution of appropriate1h-1or1r-1in THF (2 mL) was slowly added at -78C. The reaction mixture was allowed to warm slowly to 0C and stirred at the same temperature for 18 h. The reaction was quenched with 30 mL aqueous 4 M HCl and extracted with EtOAc (3 × 15 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel to afford the mixture of isomers1h-2and1r-2.

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 136618-42-3.

Reference of 141738-80-9, 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 141738-80-9 as follows.

General procedure: A mixture of 2-(3,5-dichloro-pyridin-4-yl)-7-ethynyl-4,4-dimethyl-1,4-dihydro-chromeno[3,4-d] imidazole 19a (0.1 g, 0.270 mmol), tetrabutylammonium fluoride (0.255 g, 0.810 mmol), dichlorobis- (triphenylphosphine)palladium (II) (15 mg, 0.021 mmol), 1-chloro-2-iodo-4-trifluoromethyl-benzene (0.125 g, 0.405 mmol) was heated in dry-DMSO (4.0 mL) at 80 C for 4-6 h. The reaction mass was quenched with water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, concentrated under reduced pressure and purified by flash chromatography to afford compound 20a (0.06 g, 42%) as brown solid.

According to the analysis of related databases, 141738-80-9, the application of this compound in the production field has become more and more popular.

Electric Literature of 136618-42-3, These common heterocyclic compound, 136618-42-3, name is Benzyl 4-iodobenzoate, 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 the 6-methyl-1 H-indazol-4-amine (8.26g, 54.2mmol) in dry DMF (100ml) was added iodobenzoic acid benzyl ester (19g, 56.2mmol) followed by potassium carbonate (8.15g, 59mmol), 1 /?,2/?-lambda/,lambda/’-dimethyl-1 ,2-cyclohexanediamine (0.425g, 3.0mmol) and copper (I) iodide (0.284g, 1.5mmol). The mixture was heated to 11 O0C for 5hr when LCMS showed ca. 50% conversion. Potassium carbonate (8.15g, 59mmol) was added followed by copper (I) iodide (0.284g, 1.5mmol) and 1 /?,2/?-lambda/,lambda/’-dimethyl-1 ,2-cyclohexanediamine (0.425g, 3.0mmol) and the mixture was heated to 1 1O0C for 5hr when LCMS showed absence of starting materials. The majority or the solvent was removed in vacuo and the residue was partitioned between ethyl acetate (500ml) and water (500ml). The emulsion which ensued was filtered through celite and separated. The organics were washed with saturated sodium thiosulphate solution (250ml) then brine (250ml) and dried (sodium sulphate). The mixture was filtered and concentrated in vacuo. The residue (ca. 22g) was dissolved in DCM (100ml), placed on a silica (50Og) column, pre-eluted with cyclohexane and eluted with DCM (500ml), 2% ethyl acetate/DCM (1000ml), 3% ethyl acetate/DCM (2000ml), 4% ethyl acetate/DCM (1000ml), 5% ethyl acetate/DCM (2000ml) then 10% ethyl acetate/DCM (1000ml) to give the title compound as a pale yellow solid (5.6g, 27.9%). LCMS: tRET = 3.72min, MH+ 358.1H NMR (400 MHz, CHLOROFORM-d) deltappm 8.24 (d, 2H) 8.1 1 (s, 1 H) 7.85 (d, 2H) 7.49 (d, 2H) 7.35 – 7.45 (m, 3H) 7.00 (s, 1 H) 6.32 (s, 1 H) 5.41 (s, 2H) 2.40 (s, 3H).The impure fractions (10g) were purified by CombiFlash Companion XL using a RediSep cartridge (75Og silica) eluting with a gradient of DCM/20% ethyl acetate/DCM over eight column volumes. This gave additional product (1.5g, 7.47%). 1H NMR (400 MHz, CHLOROFORM-d) deltappm 8.37 (s, 1 H) 8.22 (d, 2H) 7.99 (d, 2H)7.48 (d, 2H) 7.35 – 7.45 (m, 3H) 6.99 (s, 1 H) 6.15 (s, 1 H) 5.40 (s, 2H) 2.37 (s, 3H).

Statistics shows that Benzyl 4-iodobenzoate is playing an increasingly important role. we look forward to future research findings about 136618-42-3.