trans-3-[4-(1-benzenesulfonyl-5-methoxy-1H-indole-2-carbonyl)phenyl]acrylic acid tert-butyl ester

Base Information

• Chemical Name: trans-3-[4-(1-benzenesulfonyl-5-methoxy-1H-indole-2-carbonyl)phenyl]acrylic acid tert-butyl ester
• CAS No.: 951655-67-7
• Molecular Formula: C₂₉H₂₇NO₆S
• Molecular Weight: 517.602
• Mol file: 951655-67-7.mol

Synonyms:trans-3-[4-(1-benzenesulfonyl-5-methoxy-1H-indole-2-carbonyl)phenyl]acrylic acid tert-butyl ester

Chemical Property of trans-3-[4-(1-benzenesulfonyl-5-methoxy-1H-indole-2-carbonyl)phenyl]acrylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-3-[4-(1-benzenesulfonyl-5-methoxy-1H-indole-2-carbonyl)phenyl]acrylic acid tert-butyl ester

There total 5 articles about trans-3-[4-(1-benzenesulfonyl-5-methoxy-1H-indole-2-carbonyl)phenyl]acrylic acid tert-butyl ester 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%

4-(1-benzenesulfonyl-5-methoxy-1H-indole-2-carbonyl)benzaldehyde (951655-63-3) + (tert-butyloxycarbonylmethyl)triphenylphosphonium chloride (35000-37-4) → trans-3-[4-(1-benzenesulfonyl-5-methoxy-1H-indole-2-carbonyl)phenyl]acrylic acid tert-butyl ester (951655-67-7)

Guidance literature:

With sodium hydroxide; triethylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/jm0703136

Reference yield:

4-[1,3]dioxolan-2-ylbenzoyl chloride (951655-56-4) → trans-3-[4-(1-benzenesulfonyl-5-methoxy-1H-indole-2-carbonyl)phenyl]acrylic acid tert-butyl ester (951655-67-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

1.2: 71 percent / hexane; tetrahydrofuran / -78 - 20 °C

2.1: 81 percent / aq. HClO₄ / CH₂Cl₂ / 0 °C

3.1: 88 percent / aq. NaOH; NEt₃ / CH₂Cl₂ / 1 h / 20 °C

With sodium hydroxide; n-butyllithium; perchloric acid; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 3.1: Wittig olefination;

DOI:10.1021/jm0703136

Reference yield:

(1-benzenesulfonyl-5-methoxy-1H-indol-2-yl)-(4-[1,3]dioxolan-2-yl-phenyl)methanone (951655-60-0) → trans-3-[4-(1-benzenesulfonyl-5-methoxy-1H-indole-2-carbonyl)phenyl]acrylic acid tert-butyl ester (951655-67-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / aq. HClO₄ / CH₂Cl₂ / 0 °C

2: 88 percent / aq. NaOH; NEt₃ / CH₂Cl₂ / 1 h / 20 °C

With sodium hydroxide; perchloric acid; triethylamine; In dichloromethane; 2: Wittig olefination;

DOI:10.1021/jm0703136

upstream raw materials:

4-(1-benzenesulfonyl-5-methoxy-1H-indole-2-carbonyl)benzaldehyde

(tert-butyloxycarbonylmethyl)triphenylphosphonium chloride

4-[1,3]dioxolan-2-ylbenzoyl chloride

(1-benzenesulfonyl-5-methoxy-1H-indol-2-yl)-(4-[1,3]dioxolan-2-yl-phenyl)methanone

Downstream raw materials:

trans-3-[4-(1-benzenesulfonyl-5-methoxy-1H-indole-2-carbonyl)phenyl]acrylic acid

trans-3-[4-(5-methoxy-1H-indole-2-carbonyl)phenyl]acrylic acid

trans-3-[4-(1-benzenesulfonyl-5-methoxy-1H-indole-2-carbonyl)phenyl]-N-(tetrahydropyran-2-yloxy)acrylamide

trans-3-[4-(5-methoxy-1H-indole-2-carbonyl)phenyl]-N-(tetrahydropyran-2-yloxy)acrylamide