Category: 22726-00-7

Some common heterocyclic compound, 22726-00-7, name is 3-Bromobenzamide, molecular formula is C7H6BrNO, 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. HPLC of Formula: C7H6BrNO

A mixture of 3-bromobenzamide (3 g, 15.1 mmol), [3-(hydroxymethyl)- phenyl]boronic acid (3 g, 19.6 mmol), PdCl2(PPh3)2 (0.46 g, 0.66 mmol), and potassium carbonate (3.6 g, 26.2 mmol) in Toluene/MeOH (10:1, 40 mL) was stirred at 80 C for 18 h. The resulting black mixture was cooled to room temperature, filtered through celite, and poured into a EtO Ac/brine mixture. The two layers were separated and the aqueous was extracted with EtOAc (3x). The organics were combined, dried over sodium sulfate, filtered, and evaporated to dryness. The residue was purified by flash chromatography on silica gel eluting with a mixture of EtOAc/Hexane to give 3′-(hydroxymethyl)biphenyl-3-carboxamide as a solid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 22726-00-7, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2006/14918; (2006); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 22726-00-7 name is 3-Bromobenzamide, 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. 22726-00-7

Step 1: 3-(3-Bromophenyl)-1H-1,2,4-triazole (alternate reparation) A slurry of 3-bromobenzamide (77.4 g; 387 mmol) in DMF-DMA (150 mL) was prepared at room temperature and heated to 80 C. for 5 h. The mixture was cooled, poured into ice water (~2L) and stirred at room temperature 2 h. Precipitated solid was collected by filtration and washed with water (3*500 mL) and hexanes (2*200 mL), and the cake was air-dried on the filter. The above solid was added to a solution of hydrazine monohydrate (18.0 mL; 370 mmol) in acetic acid (500 mL) at room temperature (internal temp RT?~40 C. during addition). The mixture was stirred 5 min and heated to 90 C. for 90 min. The mixture was cooled, and partially concentrated in vacuo to approximately 100 mL. The mixture was poured into ice water (~3 L) and stirred 1 h. Precipitated solid was collected by filtration, washed with water and the cake was air-dried on the filter overnight. The solid was recrystallized from benzene, affording the title compound as a colorless solid. LC/MS (method E) tR 0.61 min, m/z 224, 226 (M+H Br isotopes).

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

Reference:
Patent; IGNAR, DIANE MICHELE; US2010/113512; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 22726-00-7, name is 3-Bromobenzamide, A new synthetic method of this compound is introduced below., 22726-00-7

To a tube charged with 3-Bromo-benzamide (180 mg, 0.9 mmol) and Pd(dppf)Cl2 (40 mg, 0.054 mmol), was added 4-Hydroxy-5-methoxy-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde (250 mg, 0.9 mmol, Example 160, step d) as a solution in 2 mL of DMF followed by the addition of K2CO3 (248 mg, 1.8 mmol) in 0.5 mL H2O. The tube was sealed with a cap and allowed to heat for 16 hours at 85 C. Reaction mixture was then filtered and purified on reverse phase HPLC. Fractions containing the desired product were combined and the solvent was removed under reduced pressure to yield 82 mg of product 2?-Formyl-5?-hydroxy-4?-methoxy-biphenyl-3-carboxylic acid amide.

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; Zhou, Jinglan; Robinson, Leslie; Gubernator, Nikolaus M.; Saiah, Eddine; Bai, Xu; Gu, Xin; US2003/225110; (2003); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics