2-(1H-Indazol-6-ylthio)-N-methyl-benzamide

Base Information

• Chemical Name: 2-(1H-Indazol-6-ylthio)-N-methyl-benzamide
• CAS No.: 944835-85-2
• Molecular Formula: C15H13N3OS
• Molecular Weight: 283.354
• UNII: WG3Q7HCW56
• Mol file: 944835-85-2.mol

Synonyms:944835-85-2;2-(1H-Indazol-6-ylthio)-N-methyl-benzamide;2-((1H-indazol-6-yl)thio)-N-methylbenzamide;2-(1H-indazol-6-ylthio)-N-methylbenzamide;2-(1H-indazol-6-ylsulfanyl)-N-methylbenzamide;Benzamide, 2-(1H-indazol-6-ylthio)-N-methyl-;Axitinib Impurity 8;WG3Q7HCW56;SCHEMBL13446109;MFCD23104312;AKOS027339737;AS-47073;F11881

Chemical Property of 2-(1H-Indazol-6-ylthio)-N-methyl-benzamide

Chemical Property:

• Boiling Point: 555.7±30.0 °C(Predicted)
• PKA: 13.02±0.40(Predicted)
• PSA: 83.08000
• Density: 1.36±0.1 g/cm3(Predicted)
• LogP: 3.46460
• Storage Temp.: 4°C, Inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 283.07793322
• Heavy Atom Count: 20
• Complexity: 352

Purity/Quality:

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

2-((1H-Indazol-6-yl)thio)-N-methylbenzamide 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC(=O)C1=CC=CC=C1SC2=CC3=C(C=C2)C=NN3
• Uses: 2-(1H-Indazol-6-ylthio)-N-methylbenzamide is a useful intermediate for the preparation of axitinib; an antitumor agent.

Technology Process of 2-(1H-Indazol-6-ylthio)-N-methyl-benzamide

There total 7 articles about 2-(1H-Indazol-6-ylthio)-N-methyl-benzamide 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: 96.0%

6-Iodo-1H-indazole (261953-36-0) + N-methyl-2-sulfanylbenzamide (20054-45-9) → 2-{(1H-indazol-6-yl)thio}-N-methylbenzamide (944835-85-2)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; cesiumhydroxide monohydrate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 100 ℃; for 4.5h; Inert atmosphere;

Reference yield: 70.0%

6-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (1266386-30-4) + N-methyl-2-sulfanylbenzamide (20054-45-9) → 2-{(1H-indazol-6-yl)thio}-N-methylbenzamide (944835-85-2)

Guidance literature:

6-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole; N-methyl-2-sulfanylbenzamide; With potassium phosphate; {NiBr₂phan2}; zinc; In water; acetone; at 45 ℃; for 24h; Inert atmosphere; Sealed tube;

With hydrogenchloride; In methanol; water; at 60 ℃;

DOI:10.1002/anie.202013017

Reference yield:

6-Iodo-1H-indazole (261953-36-0) → 2-{(1H-indazol-6-yl)thio}-N-methylbenzamide (944835-85-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: methanesulfonic acid / tetrahydrofuran; dichloromethane / 0 - 20 °C

2.1: {NiBr₂phan2}; zinc; potassium phosphate / water; acetone / 24 h / 45 °C / Inert atmosphere; Sealed tube

2.2: 60 °C

With potassium phosphate; methanesulfonic acid; {NiBr₂phan2}; zinc; In tetrahydrofuran; dichloromethane; water; acetone;

DOI:10.1002/anie.202013017

upstream raw materials:

6-Iodo-1H-indazole

N-methyl-2-sulfanylbenzamide

2,2'-dithiobis(N-methylbenzamide)

6-amino-1H-indazole

Downstream raw materials:

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

axitinib

axitinib

2-((3-iodo-1H-indazol-6-yl)thio)-N-methylbenzamide