1-benzenesulfonyl-1,4-dihydro-5H-pyrrolo[3,2-b]pyridin-5-one

Base Information

• Chemical Name: 1-benzenesulfonyl-1,4-dihydro-5H-pyrrolo[3,2-b]pyridin-5-one
• CAS No.: 677302-48-6
• Molecular Formula: C₁₃H₁₀N₂O₃S
• Molecular Weight: 274.3
• Mol file: 677302-48-6.mol

Synonyms:1-benzenesulfonyl-1,4-dihydro-5H-pyrrolo[3,2-b]pyridin-5-one

Chemical Property of 1-benzenesulfonyl-1,4-dihydro-5H-pyrrolo[3,2-b]pyridin-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-benzenesulfonyl-1,4-dihydro-5H-pyrrolo[3,2-b]pyridin-5-one

There total 4 articles about 1-benzenesulfonyl-1,4-dihydro-5H-pyrrolo[3,2-b]pyridin-5-one 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: 88.0%

1-benzenesulfonyl-5-methoxy-1H-pyrrolo[3,2-b]pyridine (372077-49-1) → 1-benzenesulfonyl-1,4-dihydro-5H-pyrrolo[3,2-b]pyridin-5-one (677302-48-6)

Guidance literature:

With chloro-trimethyl-silane; sodium iodide; In acetonitrile; at 0 ℃; Reflux;

DOI:10.1016/j.tet.2009.11.040

Reference yield:

2-methoxy-5-nitropyridine (5446-92-4) → 1-benzenesulfonyl-1,4-dihydro-5H-pyrrolo[3,2-b]pyridin-5-one (677302-48-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / potassium tert-butoxide / tetrahydrofuran / 3.5 h / -10 °C

2: 71 percent / hydrogen / palladium on charcoal / ethanol / 5 h / 20 °C / 2327.17 Torr

3: 99 percent / sodium hydroxide / benzyltriethylammonium chloride / CH₂Cl₂ / 2.25 h / 0 - 20 °C

4: 81 percent / aluminum chloride / CH₂Cl₂ / 18 h / Heating

With sodium hydroxide; aluminium trichloride; potassium tert-butylate; hydrogen; palladium on activated charcoal; N-benzyl-N,N,N-triethylammonium chloride; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1016/j.ejmech.2004.03.005

Reference yield:

2-(6-methoxy-3-nitropyridin-2-yl)acetonitrile (111795-99-4) → 1-benzenesulfonyl-1,4-dihydro-5H-pyrrolo[3,2-b]pyridin-5-one (677302-48-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 71 percent / hydrogen / palladium on charcoal / ethanol / 5 h / 20 °C / 2327.17 Torr

2: 99 percent / sodium hydroxide / benzyltriethylammonium chloride / CH₂Cl₂ / 2.25 h / 0 - 20 °C

3: 81 percent / aluminum chloride / CH₂Cl₂ / 18 h / Heating

With sodium hydroxide; aluminium trichloride; hydrogen; palladium on activated charcoal; N-benzyl-N,N,N-triethylammonium chloride; In ethanol; dichloromethane;

DOI:10.1016/j.ejmech.2004.03.005

upstream raw materials:

1-benzenesulfonyl-5-methoxy-1H-pyrrolo[3,2-b]pyridine

2-methoxy-5-nitropyridine

2-(6-methoxy-3-nitropyridin-2-yl)acetonitrile

5-methoxy-4-aza-1H-indole

Downstream raw materials:

1-benzenesulfonyl-5-(5-bromopentyloxy)-1H-pyrrolo[3,2-b]pyridine

1-benzenesulfonyl-5-(6-bromohexyloxy)-1H-pyrrolo[3,2-b]pyridine

trifluoromethanesulfonic acid 1-benzenesulfonyl-1H-pyrrolo[3,2-b]pyridin-5-yl ester

1,6-bis[(1-benzenesulfonyl-1H-pyrrolo[3,2-b]pyridin-5-yl)oxy]hexane

Refernces

• 1、 Larraya, Carlos,Guillard, Jerome,Renard, Pierre,Audinot, Valerie,Boutin, Jean A.,Delagrange, Philippe,Bennejean, Caroline,Viaud-Massuard, Marie-Claude. "Preparation of 4-azaindole and 7-azaindole dimers with a bisalkoxyalkyl spacer in order to preferentially target melatonin MT1 receptors over melatonin MT2 receptors". . p. 515 - 526. Retrieved 2007/10/03.