4-[4-allyl-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-but-3-en-2-one

Base Information

• Chemical Name: 4-[4-allyl-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-but-3-en-2-one
• CAS No.: 333303-42-7
• Molecular Formula: C₂₂H₂₁NO₃S
• Molecular Weight: 379.48
• Mol file: 333303-42-7.mol

Synonyms:4-[4-allyl-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-but-3-en-2-one

Chemical Property of 4-[4-allyl-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-but-3-en-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[4-allyl-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-but-3-en-2-one

There total 4 articles about 4-[4-allyl-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-but-3-en-2-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: 81.0%

methyl vinyl ketone (78-94-4,25038-87-3) + 4-allyl-3-bromo-1-(toluene-4-sulfonyl)-1H-indole (333303-41-6) → 4-[4-allyl-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-but-3-en-2-one (333303-42-7)

Guidance literature:

With palladium diacetate; triethylamine; triphenylphosphine; In dimethyl sulfoxide; at 90 ℃;

DOI:10.1016/S0040-4039(00)02194-8

Reference yield:

3-bromo-1-(4-methylbenzenesulfonyl)-1H-indole (90481-77-9) → 4-[4-allyl-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-but-3-en-2-one (333303-42-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Hg(OAc)2; HClO₄ / acetic acid / 48 h / 20 °C

1.2: saturated NaCl / acetic acid / 0.25 h

1.3: I₂ / CH₂Cl₂ / 16 h / 20 °C

2.1: 76 percent / Pd(Ph₃P)4/BHA / toluene / 90 °C

3.1: 81 percent / Pd(OAc)2; Ph₃P; Et₃N / dimethylsulfoxide / 90 °C

With palladium diacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; perchloric acid; 3-tert-Butyl-4-hydroxyanisole; mercury(II) diacetate; triethylamine; triphenylphosphine; In acetic acid; dimethyl sulfoxide; toluene; 2.1: Stille coupling / 3.1: Heck reaction;

DOI:10.1016/S0040-4039(00)02194-8

Reference yield:

3-bromo-4-N-p-toluenesulfonylindole (333303-40-5) → 4-[4-allyl-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-but-3-en-2-one (333303-42-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / Pd(Ph₃P)4/BHA / toluene / 90 °C

2: 81 percent / Pd(OAc)2; Ph₃P; Et₃N / dimethylsulfoxide / 90 °C

With palladium diacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 3-tert-Butyl-4-hydroxyanisole; triethylamine; triphenylphosphine; In dimethyl sulfoxide; toluene; 1: Stille coupling / 2: Heck reaction;

DOI:10.1016/S0040-4039(00)02194-8

upstream raw materials:

methyl vinyl ketone

4-allyl-3-bromo-1-(toluene-4-sulfonyl)-1H-indole

3-bromo-1-(4-methylbenzenesulfonyl)-1H-indole

3-bromo-4-N-p-toluenesulfonylindole

Downstream raw materials:

4-allyl-3-(3-methyl-buta-1,3-dienyl)-1-(toluene-4-sulfonyl)-1H-indole