Benzamide, 2-[(3-iodo-1H-indazol-6-yl)thio]-N-methyl-

Base Information

• Chemical Name: Benzamide, 2-[(3-iodo-1H-indazol-6-yl)thio]-N-methyl-
• CAS No.: 885126-34-1
• Molecular Formula: C15H12IN3OS
• Molecular Weight: 409.25
• Hs Code.: 2933998090
• Mol file: 885126-34-1.mol

Synonyms:Benzamide,2-(3-iodo-1H-indazol-6-yl)thio-N-methyl;2-(3-Iodo-1H-indazol-6-ylsulfanyl)-N-methyl-benzamide;2-[(3-Iodo-1H-indazol-6-yl)thio]-N-methylbenzamide;

Chemical Property of Benzamide, 2-[(3-iodo-1H-indazol-6-yl)thio]-N-methyl-

Chemical Property:

• Boiling Point: 613.9±45.0 °C(Predicted)
• PKA: 11.06±0.40(Predicted)
• PSA: 83.08000
• Density: 1.80±0.1 g/cm3(Predicted)
• LogP: 4.06920

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-((3-Iodo-1H-indazol-6-yl)thio)-N-methylbenzamide 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzamide, 2-[(3-iodo-1H-indazol-6-yl)thio]-N-methyl-

There total 10 articles about Benzamide, 2-[(3-iodo-1H-indazol-6-yl)thio]-N-methyl- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

2-{(1H-indazol-6-yl)thio}-N-methylbenzamide (944835-85-2) → 2-((3-iodo-1H-indazol-6-yl)thio)-N-methylbenzamide (885126-34-1)

Guidance literature:

With iodine; potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 4h;

Reference yield: 65.0%

6-Iodo-1H-indazole (261953-36-0) + N-methyl-2-sulfanylbenzamide (20054-45-9) → 2-((3-iodo-1H-indazol-6-yl)thio)-N-methylbenzamide (885126-34-1)

Guidance literature:

6-Iodo-1H-indazole; With copper(II) acetate hydrate; potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 80 ℃; Inert atmosphere; Large scale;

N-methyl-2-sulfanylbenzamide; In 1-methyl-pyrrolidin-2-one; at 80 - 105 ℃; for 1.75h; Large scale;

With iodine; In 1-methyl-pyrrolidin-2-one; at 105 ℃; for 2h; Large scale;

Reference yield:

6-Iodo-1H-indazole (261953-36-0) → 2-((3-iodo-1H-indazol-6-yl)thio)-N-methylbenzamide (885126-34-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium hydrogencarbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1-methyl-pyrrolidin-2-one / 0.5 h / 25 °C / Inert atmosphere; Large scale

1.2: 3 h / 25 - 50 °C / Inert atmosphere; Large scale

2.1: iodine; potassium hydroxide / 1-methyl-pyrrolidin-2-one; water / 5.5 h / 25 °C / Inert atmosphere; Large scale

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; iodine; sodium hydrogencarbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; potassium hydroxide; In 1-methyl-pyrrolidin-2-one; water; 1.1: |Stille Cross-Coupling (Migita-Kosugi-Stille Coupling) / 1.2: |Stille Cross-Coupling (Migita-Kosugi-Stille Coupling);

DOI:10.1021/op400088k

upstream raw materials:

3,6-diiodoindazole

N-methyl-2-sulfanylbenzamide

2-{(1H-indazol-6-yl)thio}-N-methylbenzamide

6-Iodo-1H-indazole

Downstream raw materials:

N-1 THP-protected 2-(3-iodo-1H-indazol-6-ylsulfanyl)-N-methyl-benzamide

N-1 Boc 2-(3-iodo-1H-indazol-6-ylsulfanyl)-N-methyl-benzamide

axitinib

N-methyl-2-((1-acetyl-3-((1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide

Refernces

• 1、 -. "PROCESS FOR PREPARING AXITINIB, PROCESS FOR PURIFYING THE INTERMEDIATE 2-((3-IODO-1H-INDAZOL-6-YL)THIO)-N-METHYLBENZAMIDE, PROCESS FOR PURIFYING AXITINIB VIA THE AXITINIB HCL SALT, SOLID FORM OF THE AXITINIB HCL SALT". Page/Page column 23-24. . Retrieved 2020/10/28.
• 2、 Shen, Chao,Shen, Hongyun,Yang, Ming,Xia, Chengcai,Zhang, Pengfei. "A novel D-glucosamine-derived pyridyltriazole@ palladium catalyst for solvent-free Mizoroki-Heck reactions and its application in the synthesis of Axitinib". . p. 225 - 230. Retrieved 2018/04/16.