3-Iodo-1H-indazole-6-carbonitrile

Base Information

• Chemical Name: 3-Iodo-1H-indazole-6-carbonitrile
• CAS No.: 906000-39-3
• Molecular Formula: C8H4IN3
• Molecular Weight: 269.044
• Hs Code.: 2933998090
• European Community (EC) Number: 813-503-2
• DSSTox Substance ID: DTXSID50694599
• Wikidata: Q82623756
• Mol file: 906000-39-3.mol

Synonyms:3-Iodo-1H-indazole-6-carbonitrile;906000-39-3;3-iodo-2H-indazole-6-carbonitrile;3-Iodo-6-cyano (1H)indazole;SCHEMBL4155921;DTXSID50694599;FRYOUXROKRKPQP-UHFFFAOYSA-N;AMY15842;MFCD10696802;AB58208;CS-0054303;EN300-3168560;A860753;J-512672

Chemical Property of 3-Iodo-1H-indazole-6-carbonitrile

Chemical Property:

• PSA: 52.47000
• LogP: 2.03918
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 268.94499
• Heavy Atom Count: 12
• Complexity: 222

Purity/Quality:

97% ^*data from raw suppliers

3-Iodo-1H-indazole-6-carbonitrile 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(NN=C2C=C1C#N)I

Technology Process of 3-Iodo-1H-indazole-6-carbonitrile

There total 1 articles about 3-Iodo-1H-indazole-6-carbonitrile 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:

6-bromo-1H-indazole (79762-54-2) → 3-iodo-1H-indazole-6-carbonitrile (906000-39-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; N,N,N,N,-tetramethylethylenediamine / N,N-dimethyl-formamide / 0.08 h / 160 °C / Microwave irradiation

2: potassium hydroxide; iodine / N,N-dimethyl-formamide / 2.5 h / 20 °C

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; N,N,N,N,-tetramethylethylenediamine; iodine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; potassium hydroxide; In N,N-dimethyl-formamide;

Reference yield: 69.0%

methanol (67-56-1) + 3-iodo-1H-indazole-6-carbonitrile (906000-39-3) + carbon monoxide (201230-82-2) → methyl 6-cyano-1H-indazole-3-carboxylate (885279-07-2)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; triethylamine; In toluene; at 80 ℃; under 750.075 Torr; Autoclave;

DOI:10.1055/s-0030-1260199

Reference yield:

3-iodo-1H-indazole-6-carbonitrile (906000-39-3) → N-(2-(6-cyano-1H-indazol-3-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)-N-methylbenzamide

Guidance literature:

Multi-step reaction with 5 steps

1.1: iodine; ethyl bromide; magnesium / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

1.2: 0.67 h / 0 °C / Inert atmosphere

2.1: dmap / tetrahydrofuran / 0.5 h / 20 °C

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide / toluene / 24 h / 95 °C / Inert atmosphere

4.1: hydrogenchloride / ethanol; water / 5 h / 20 °C

5.1: pyridine / 60 °C

With pyridine; hydrogenchloride; dmap; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; ethyl bromide; iodine; magnesium; In tetrahydrofuran; diethyl ether; ethanol; water; toluene; 3.1: |Stille Cross Coupling;

DOI:10.1016/j.bmc.2015.02.004

upstream raw materials:

6-bromo-1H-indazole

Downstream raw materials:

methyl 6-cyano-1H-indazole-3-carboxylate