3-BROMO-5-METHOXY (1H)INDAZOLE

Base Information

• Chemical Name: 3-BROMO-5-METHOXY (1H)INDAZOLE
• CAS No.: 885519-30-2
• Molecular Formula: C8H7BrN2O
• Molecular Weight: 227.06
• Hs Code.: 2933990090
• Mol file: 885519-30-2.mol

Synonyms:3-BROMO-5-METHOXY (1H)INDAZOLE;1H-INDAZOLE,3-BROMO-5-METHOXY-

Chemical Property of 3-BROMO-5-METHOXY (1H)INDAZOLE

Chemical Property:

• Melting Point: 178 °C
• Boiling Point: 370.3±22.0 °C(Predicted)
• PKA: 11.43±0.40(Predicted)
• PSA: 37.91000
• Density: 1.678±0.06 g/cm3(Predicted)
• LogP: 2.33400
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

NLT 98% ^*data from raw suppliers

3-Bromo-5-methoxy-1H-indazole ^*data from reagent suppliers

Safty Information:

• Statements: 20/21/22
• Safety Statements: 24/25-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-BROMO-5-METHOXY (1H)INDAZOLE

There total 2 articles about 3-BROMO-5-METHOXY (1H)INDAZOLE 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: 45.0%

5-methoxy-1H-indazole (94444-96-9) → 3-bromo-5-methoxy-1H-indazole (885519-30-2)

Guidance literature:

With bromine; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1055/s-0030-1260110

Reference yield:

2-methyl-4-methoxyaniline (102-50-1) → 3-bromo-5-methoxy-1H-indazole (885519-30-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaNO₂; AcOH

1.2: Et₃N

2.1: N-bromosuccinimide; KOH

With potassium hydroxide; N-Bromosuccinimide; acetic acid; sodium nitrite;

DOI:10.1016/j.bmcl.2005.08.049

Reference yield:

3-bromo-5-methoxy-1H-indazole (885519-30-2) → 4-[5-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl]piperazin-1-carboxylic acid benzyl ester (1339955-96-2)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / ethyl acetate / Reflux

2: palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 7 h / Sealed tube; Inert atmosphere; Reflux

With palladium diacetate; caesium carbonate; toluene-4-sulfonic acid; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; ethyl acetate; 2: Buchwald-Hartwig C-N coupling reaction;

DOI:10.1055/s-0030-1260110

upstream raw materials:

5-methoxy-1H-indazole

2-methyl-4-methoxyaniline

Downstream raw materials:

3-bromo-5-methoxy-indazole-1-carboxylic acid tert-butyl ester

4-[5-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl]piperazin-1-carboxylic acid benzyl ester

Refernces

• 1、 Vasudevan, Anil,Souers, Andrew J.,Freeman, Jennifer C.,Verzal, Mary K.,Gao, Ju,Mulhern, Mathew M.,Wodka, Derek,Lynch, John K.,Engstrom, Kenneth M.,Wagaw, Seble H.,Brodjian, Sevan,Dayton, Brian,Falls, Doug H.,Bush, Eugene,Brune, Michael,Shapiro, Robin D.,Marsh, Kennan C.,Hernandez, Lisa E.,Collins, Christine A.,Kym, Philip R.. "Aminopiperidine indazoles as orally efficacious melanin concentrating hormone receptor-1 antagonists". . p. 5293 - 5297. Retrieved 2007/10/03.