5-benzenesulfonyl-8-hydroxy-7-methoxy-2-phenylmethanesulfonyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Base Information

• Chemical Name: 5-benzenesulfonyl-8-hydroxy-7-methoxy-2-phenylmethanesulfonyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
• CAS No.: 267666-27-3
• Molecular Formula: C₂₅H₂₄N₂O₆S₂
• Molecular Weight: 512.607
• Mol file: 267666-27-3.mol

Synonyms:5-benzenesulfonyl-8-hydroxy-7-methoxy-2-phenylmethanesulfonyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Chemical Property of 5-benzenesulfonyl-8-hydroxy-7-methoxy-2-phenylmethanesulfonyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-benzenesulfonyl-8-hydroxy-7-methoxy-2-phenylmethanesulfonyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

There total 5 articles about 5-benzenesulfonyl-8-hydroxy-7-methoxy-2-phenylmethanesulfonyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole 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: 85.0%

4-methoxy-1-phenylmethanesulfonyl-1,2,3,6-tetrahydro-pyridine (267666-14-8) + N-(3-methoxy-4-oxo-cyclohexa-2,5-dienylidene)-benzenesulfonamide → 5-benzenesulfonyl-8-hydroxy-7-methoxy-2-phenylmethanesulfonyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (267666-27-3)

Guidance literature:

With titanium(IV) isopropylate; titanium tetrachloride; In dichloromethane; at -78 ℃;

DOI:10.1021/jo9916176

Reference yield:

4-piperidone hydrochloride (41979-39-9) → 5-benzenesulfonyl-8-hydroxy-7-methoxy-2-phenylmethanesulfonyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (267666-27-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / K₂CO₃ / H₂O; CHCl₃ / 20 °C

2: p-TsOH*H₂O / 10 h

3: 62 percent / AlCl₃; Et₃N / diethyl ether / 20 °C

4: 85 percent / TiCl₄; Ti(OiPr)4 / CH₂Cl₂ / -78 °C

With titanium(IV) isopropylate; aluminium trichloride; titanium tetrachloride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; In diethyl ether; dichloromethane; chloroform; water; 1: Substitution / 2: Addition / 3: Elimination / 4: Elimination;

DOI:10.1021/jo9916176

Reference yield:

4,4-dimethoxy-1-phenylmethanesulfonyl-piperidine (958752-68-6) → 5-benzenesulfonyl-8-hydroxy-7-methoxy-2-phenylmethanesulfonyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (267666-27-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 62 percent / AlCl₃; Et₃N / diethyl ether / 20 °C

2: 85 percent / TiCl₄; Ti(OiPr)4 / CH₂Cl₂ / -78 °C

With titanium(IV) isopropylate; aluminium trichloride; titanium tetrachloride; triethylamine; In diethyl ether; dichloromethane; 1: Elimination / 2: Elimination;

DOI:10.1021/jo9916176

upstream raw materials:

4-methoxy-1-phenylmethanesulfonyl-1,2,3,6-tetrahydro-pyridine

4-piperidone hydrochloride

1-(benzylsulfonyl)piperidin-4-one

4,4-dimethoxy-1-phenylmethanesulfonyl-piperidine

Downstream raw materials:

trifluoromethanesulfonic acid 5-benzenesulfonyl-7-methoxy-2-phenylmethanesulfonyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-8-yl ester

5-benzenesulfonyl-7,8-dimethoxy-2-phenylmethanesulfonyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole