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

Base Information

• Chemical Name: 2-((3-Iodo-1H-indazol-6-yl)thio)-N-methylbenzamide
• CAS No.: 885126-34-1
• Molecular Formula: C15H12IN3OS
• Molecular Weight: 409.25
• Hs Code.: 2933998090
• UNII: W47EP2H8YZ
• DSSTox Substance ID: DTXSID30470338
• Wikidata: Q72483714
• Mol file: 885126-34-1.mol

Synonyms:885126-34-1;2-((3-Iodo-1H-indazol-6-yl)thio)-N-methylbenzamide;Benzamide, 2-[(3-iodo-1H-indazol-6-yl)thio]-N-methyl-;2-[(3-iodo-2H-indazol-6-yl)sulfanyl]-N-methylbenzamide;2-[(3-Iodo-1H-indazol-6-yl)sulfanyl]-N-methylbenzamide;2-[(3-Iodo-1H-indazol-6-yl)thio]-N-methylbenzamide;C15H12IN3OS;W47EP2H8YZ;Benzamide,2-(3-iodo-1H-indazol-6-yl)thio-N-methyl-;SCHEMBL2830790;DTXSID30470338;VHZLHFNNNDGPLF-UHFFFAOYSA-N;SB16362;F17894;A851928;2-(3-iodo-1H-indazol-6-ylthio)-N-methylbenzamide;2(3Iodo-1H-indazol-6-ylsulfanyl)-N-methyl-benzamide;2-(3-Iodo-1H-indazol-6-ylsulfanyl)-N-methyl-benzamide

Chemical Property of 2-((3-Iodo-1H-indazol-6-yl)thio)-N-methylbenzamide

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
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 408.97458
• Heavy Atom Count: 21
• Complexity: 384

Purity/Quality:

97% ^*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:

• Canonical SMILES: CNC(=O)C1=CC=CC=C1SC2=CC3=NNC(=C3C=C2)I

Technology Process of 2-((3-Iodo-1H-indazol-6-yl)thio)-N-methylbenzamide

There total 10 articles about 2-((3-Iodo-1H-indazol-6-yl)thio)-N-methylbenzamide 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

6-[2-(methylcarbamoyl)phenylsulfanyl]-3-[2-(pyridine-2-yl)ethynyl]indazole