Category: 136618-42-3

Electric Literature of 136618-42-3, A common heterocyclic compound, 136618-42-3, name is Benzyl 4-iodobenzoate, molecular formula is C14H11IO2, 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.

Intermediate 8: Phenvlmethvl 4-(4-amino-6-methvl-1H-indazol-1-vl)benzoate; 6-Methyl-1 W-indazol-4-amine (5.48g, 37.3mmol), copper (I) iodide (71 mg, 0.37mmol), trans-1 ,2-cyclohexanediamine (420mg, 0.37mmol) and tripotassium phosphate (16.6g, 78.3mmol) were added to a solution of phenylmethyl 4-iodobenzoate (12.61g, 37.3mmol) in 1 ,4-dioxane (2OmL). More 1 ,4-dioxane (3OmL) was added and the mixture heated under reflux for 3 hours 15 min and then allowed to gradually cool to room temperature and partitioned between water and ethyl acetate. The aqueous phase was extracted once more with ethyl acetate and the combined organic extracts were washed with brine and dried and evaporated to give a brown solid (13.58g). This crude product was combined with material (0.66g) from a similar reaction and purified by column chromatography on silica gel (Merck 7734, 50OmL) eluting initially with 10% and finally with 20% ethyl acetate in dichloromethane. Evaporation of product containing fractions gave a brown-yellow solid (5.12g) which was dissolved in ethyl acetate (4OmL) at 60 and warm cyclohexane (7OmL) was added. The mixture was then cooled in ice and the precipitate was collected by filtration, washed with cyclohexane:ethyl acetate (4:1 , 4OmL) and dried to give the title compound as a beige solid (4.29g). LCMS (System A): tRET = 3.77 min; MNH4+ = 358

The synthetic route of 136618-42-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/50243; (2009); 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. 136618-42-3, name is Benzyl 4-iodobenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C14H11IO2

Intermediate 2: Phenylmethyl 4-(4-amino-6-methyl-1/-/-indazol-1-yl)benzoate; 6-Methyl-1 H-indazol-4-amine (5.48g, 37.3mmol), copper (I) iodide (71 mg, 0.37mmol), frans-i ^-cyclohexanediamine (420mg, 0.37mrnol) and tripotassium phosphate (16.6g, 78.3mmol) were added to a solution of phenylmethyl 4-iodobenzoate (12.61g, 37.3mmol) in 1 ,4-dioxane (2OmL). More 1 ,4-dioxane (3OmL) was added and the mixture heated under reflux for 3 hours 15 min and then allowed to gradually cool to room temperature and partitioned between water and ethyl acetate. The aqueous phase was extracted once more with ethyl acetate and the combined organic extracts were washed with brine and dried and evaporated to give a brown solid (13.58g). This crude product was combined with material (0.66g) from a similar reaction and purified by column chromatography on silica gel (Merck 7734, 50OmL) eluting initially with 10% and finally with 20% ethyl acetate in dichloromethane. Evaporation of product containing fractions gave a brown-yellow solid (5.12g) which was dissolved in ethyl acetate (4OmL) at 60 and warm cyclohexane (7OmL) was added. The mixture was then cooled in ice and the precipitate was collected by filtration, washed with cyclohexane:ethyl acetate (4:1 , 4OmL) and dried to give the title compound as a beige solid (4.29g). LCMS (System A): tRET = 3.77; MNH4+ = 358

The synthetic route of 136618-42-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/50220; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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.

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.

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. 136618-42-3, name is Benzyl 4-iodobenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 136618-42-3

Intermediate 8: Phenylmethyl 4-(4-amJno-6-methyl-1 H-indazol-1-yl)benzoate; 6-Methyl-1 /-/-indazol-4-amine (5.48g, 37.3mmol), copper (I) iodide (71 mg, 0.37mmol), frans-1 ,2-cyclohexanediamine (420mg, 0.37mmol) and tripotassium phosphate (16.6g, 78.3mmol) were added to a solution of phenylmethyl 4-iodobenzoate (12.61g, 37.3mmol) in 1 ,4-dioxane (2OmL). More 1 ,4-dioxane (3OmL) was added and the mixture heated under reflux for 3 hours 15 min and then allowed to gradually cool to room temperature and partitioned between water and ethyl acetate. The aqueous phase was extracted once more with ethyl acetate and the combined organic extracts were washed with brine and dried and evaporated to give a brown solid (13.58g). This crude product was combined with material (0.66g) from a similar reaction and purified by column chromatography on silica gel (Merck 7734, 50OmL) eluting initially with 10% and finally with 20% ethyl acetate in dichloromethane. Evaporation of product containing fractions gave a brown-yellow solid (5.12g) which was dissolved in ethyl acetate (4OmL) at 60 and warm cyclohexane (7OmL) was added. The mixture was then cooled in ice and the precipitate was collected by filtration, washed with cyclohexane:ethyl acetate (4:1 , 4OmL) and dried to give the title compound as a beige solid (4.29g). LCMS (System A): tRET = 3.77 min; MNH4+ = 358

The synthetic route of 136618-42-3 has been constantly updated, and we look forward to future research findings.