tert-butyl 4-(1-tosyl-1H-indol-3-yl)pent-4-enoate

Base Information

• Chemical Name: tert-butyl 4-(1-tosyl-1H-indol-3-yl)pent-4-enoate
• CAS No.: 1338575-78-2
• Molecular Formula: C₂₄H₂₇NO₄S
• Molecular Weight: 425.549
• Mol file: 1338575-78-2.mol

Synonyms:tert-butyl 4-(1-tosyl-1H-indol-3-yl)pent-4-enoate

Chemical Property of tert-butyl 4-(1-tosyl-1H-indol-3-yl)pent-4-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 4-(1-tosyl-1H-indol-3-yl)pent-4-enoate

There total 2 articles about tert-butyl 4-(1-tosyl-1H-indol-3-yl)pent-4-enoate 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: 73.0%

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-p-toluenesulfonyl-1H-indole (1073354-51-4) + 4-bromo-4-pentenoic acid tert-butyl ester (92975-38-7) → tert-butyl 4-(1-tosyl-1H-indol-3-yl)pent-4-enoate (1338575-78-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; lithium chloride; In ethanol; toluene; at 100 ℃; for 3h; Inert atmosphere;

DOI:10.1021/ol202436a

Reference yield:

acetic acid tert-butyl ester (540-88-5) → tert-butyl 4-(1-tosyl-1H-indol-3-yl)pent-4-enoate (1338575-78-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 °C / Inert atmosphere

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; lithium chloride / ethanol; toluene / 3 h / 100 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; ethanol; toluene; 2.1: Suzuki coupling;

DOI:10.1021/ol202436a

Reference yield: 62.0%

tert-butyl 4-(1-tosyl-1H-indol-3-yl)pent-4-enoate (1338575-78-2) + p-nitrobenzenesulfonamide (6325-93-5) → 4-nitro-N-((5-oxo-2-(1-tosyl-1H-indol-3-yl)tetrahydrofuran-2-yl)methyl)benzenesulfonamide (1338575-89-5)

Guidance literature:

tert-butyl 4-(1-tosyl-1H-indol-3-yl)pent-4-enoate; With tetrakis(actonitrile)copper(I) hexafluorophosphate; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline]; In acetonitrile; at 20 ℃; for 0.166667h; Molecular sieve; Inert atmosphere;

p-nitrobenzenesulfonamide; With iodosylbenzene; In acetonitrile; at 20 ℃; for 48h; Inert atmosphere;

DOI:10.1021/ol202436a

upstream raw materials:

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-p-toluenesulfonyl-1H-indole

4-bromo-4-pentenoic acid tert-butyl ester

acetic acid tert-butyl ester

Downstream raw materials:

4-nitro-N-((5-oxo-2-(1-tosyl-1H-indol-3-yl)tetrahydrofuran-2-yl)methyl)benzenesulfonamide