1082041-53-9

Basic information

• Product Name: 6-Iodo-3-methyl-1H-indazole
• Synonyms: 6-Iodo-3-methyl-1H-indazole;6-Iodo-3-Methyl-1H-indazo...;1H-Indazole, 6-iodo-3-Methyl-
• CAS NO: 1082041-53-9
• Molecular Formula: C8H7IN2
• Molecular Weight: 258.05905
• Mol File: 1082041-53-9.mol
• Article Data: 0

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-Iodo-3-methyl-1H-indazole(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Iodo-3-methyl-1H-indazole(1082041-53-9)
• EPA Substance Registry System: 6-Iodo-3-methyl-1H-indazole(1082041-53-9)

Safety Data

• Hazardous Substances Data: 1082041-53-9(Hazardous Substances Data)

Usage

General Description

6-Iodo-3-methyl-1H-indazole is a chemical compound with the molecular formula C9H8IN. It is an indazole derivative with a substitution of an iodo group at the 6th position and a methyl group at the 3rd position. 6-Iodo-3-methyl-1H-indazole has been of interest in medicinal chemistry and research due to its potential pharmaceutical applications, particularly in the development of new drugs. Indazole derivatives are known to exhibit a wide range of biological activities, including anti-inflammatory, anti-cancer, and anti-microbial properties. The introduction of an iodo group and methyl group to the indazole structure may alter its pharmacological properties and contribute to its potential therapeutic benefits. Additionally, the presence of an iodo group also makes this compound useful for labeling studies in biochemistry and molecular biology.

Synthetic route

3,4-dihydro-2H-pyran (110-87-2) + C8H7IN2 (1082041-53-9) → 6-iodo-3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

Conditions	Yield
With methanesulfonic acid In tetrahydrofuran at 80℃; for 8h; Inert atmosphere;	81%

C8H7IN2 (1082041-53-9) + methyl 2,2,2-trichloroacetimidate (2533-69-9) → 6-iodo-2,3-dimethyl-2H-indazole (1234616-58-0)

Conditions	Yield
Stage #1: C8H7IN2 With trifluorormethanesulfonic acid In dichloromethane at 25 - 35℃; Inert atmosphere; Stage #2: methyl 2,2,2-trichloroacetimidate In dichloromethane at 20℃; Inert atmosphere; regioselective reaction;

C8H7IN2 (1082041-53-9) → 3-((3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl)thio)propanoic acid

Conditions

Yield

Multi-step reaction with 3 steps 1: methanesulfonic acid / tetrahydrofuran / 8 h / 80 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / N,N-dimethyl acetamide / 2 h / 150 °C / Inert atmosphere 3: lithium hydroxide; water / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere View Scheme

C8H7IN2 (1082041-53-9) → 3-((3-methyl-1H-indazol-6-yl)thio)-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)propanamide

Conditions

Yield

Multi-step reaction with 5 steps 1: methanesulfonic acid / tetrahydrofuran / 8 h / 80 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / N,N-dimethyl acetamide / 2 h / 150 °C / Inert atmosphere 3: lithium hydroxide; water / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere 4: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 2 h / 20 °C 5: trifluoroacetic acid / dichloromethane / 4 h / 20 °C View Scheme

C8H7IN2 (1082041-53-9) → methyl 3-((3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl)thio)propanoate

Conditions	Yield
Multi-step reaction with 2 steps 1: methanesulfonic acid / tetrahydrofuran / 8 h / 80 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / N,N-dimethyl acetamide / 2 h / 150 °C / Inert atmosphere View Scheme

C8H7IN2 (1082041-53-9) → C29H36F3N5O2S

Conditions

Yield

Multi-step reaction with 4 steps 1: methanesulfonic acid / tetrahydrofuran / 8 h / 80 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / N,N-dimethyl acetamide / 2 h / 150 °C / Inert atmosphere 3: lithium hydroxide; water / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere 4: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 2 h / 20 °C View Scheme

Downstream Products

• 1234616-58-0 6-iodo-2,3-dimethyl-2H-indazole