(R)-N-[9-(2-cyanoethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-4-fluorobenzenesulfonamide

Base Information

• Chemical Name: (R)-N-[9-(2-cyanoethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-4-fluorobenzenesulfonamide
• CAS No.: 118699-38-0
• Molecular Formula: C₂₁H₂₀FN₃O₂S
• Molecular Weight: 397.473
• Mol file: 118699-38-0.mol

Synonyms:(R)-N-[9-(2-cyanoethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-4-fluorobenzenesulfonamide

Chemical Property of (R)-N-[9-(2-cyanoethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-4-fluorobenzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (R)-N-[9-(2-cyanoethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-4-fluorobenzenesulfonamide

There total 22 articles about (R)-N-[9-(2-cyanoethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-4-fluorobenzenesulfonamide 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: 67.0%

acrylonitrile (107-13-1,25014-41-9) + (R)-4-fluoro-N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)benzenesulfonamide (116650-36-3) → (R)-N-[9-(2-cyanoethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-4-fluorobenzenesulfonamide (118699-38-0)

Guidance literature:

(R)-4-fluoro-N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)benzenesulfonamide; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 0.0833333h;

acrylonitrile; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1021/jo300552v

Reference yield:

N-[9-(2-cyanoethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-4-fluorobenzenesulfonamide → (R)-N-[9-(2-cyanoethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-4-fluorobenzenesulfonamide (118699-38-0) + (S)-N-[9-(2-cyanoethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-4-fluorobenzenesulfonamide (134525-56-7)

Guidance literature:

With chiralpak IC; In hexane; isopropyl alcohol; at 40 ℃; Resolution of racemate;

DOI:10.1021/jo300552v

Reference yield:

1,2,3,4-tetrahydrocarbazol-3-one (51145-61-0) → (R)-N-[9-(2-cyanoethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-4-fluorobenzenesulfonamide (118699-38-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: D-glucose / water / 24 h / 30 °C / Enzymatic reaction

2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere

2.2: 10 h / -25 - -15 °C

3.1: water; triphenylphosphine / 15 h / 65 °C

4.1: triethylamine / dichloromethane / 1 h / 20 °C

5.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C

5.2: 1 h / 20 °C

With D-glucose; water; sodium hydride; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 2.1: Mitsunobu reaction / 2.2: Mitsunobu reaction / 3.1: Staudinger reaction;

DOI:10.1021/jo300552v

upstream raw materials:

cyclohexanedione monoethylene ketal

(S)-2,3,4,9-tetrahydro-1H-carbazol-3-yl methanesulfonate

4-fluoro-N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)benzenesulfonamide

(S)-(-)-2,3,4,9-tetrahydro-1H-carbazol-3-ol

Downstream raw materials:

ramatroban