7-[2-(3-bromo-4-hydroxyphenyl)-1-(triisopropylsilyloxymethyl)ethylamino]-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-pyrrolo[4,3,2-de]quinolin-8-one

Base Information

• Chemical Name: 7-[2-(3-bromo-4-hydroxyphenyl)-1-(triisopropylsilyloxymethyl)ethylamino]-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-pyrrolo[4,3,2-de]quinolin-8-one
• CAS No.: 613223-70-4
• Molecular Formula: C₃₅H₄₄BrN₃O₅SSi
• Molecular Weight: 726.807
• Mol file: 613223-70-4.mol

Synonyms:7-[2-(3-bromo-4-hydroxyphenyl)-1-(triisopropylsilyloxymethyl)ethylamino]-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-pyrrolo[4,3,2-de]quinolin-8-one

Chemical Property of 7-[2-(3-bromo-4-hydroxyphenyl)-1-(triisopropylsilyloxymethyl)ethylamino]-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-pyrrolo[4,3,2-de]quinolin-8-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-[2-(3-bromo-4-hydroxyphenyl)-1-(triisopropylsilyloxymethyl)ethylamino]-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-pyrrolo[4,3,2-de]quinolin-8-one

There total 6 articles about 7-[2-(3-bromo-4-hydroxyphenyl)-1-(triisopropylsilyloxymethyl)ethylamino]-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-pyrrolo[4,3,2-de]quinolin-8-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: 55.0%

7-Methoxy-1-<(4-methylphenyl)sulfonyl>-3,4-dihydropyrrolo<4,3,2-de>quinolin-8(1H)-one (153718-76-4) + [2-[3-bromo-4-hydroxyphenyl]-1-(triisopropylsilyloxymethyl)ethyl]tritylamine (613223-77-1) → 7-[2-(3-bromo-4-hydroxyphenyl)-1-(triisopropylsilyloxymethyl)ethylamino]-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-pyrrolo[4,3,2-de]quinolin-8-one (613223-70-4)

Guidance literature:

[2-[3-bromo-4-hydroxyphenyl]-1-(triisopropylsilyloxymethyl)ethyl]tritylamine; With hydrogenchloride; In methanol; at 20 ℃; for 0.5h;

7-Methoxy-1-<(4-methylphenyl)sulfonyl>-3,4-dihydropyrrolo<4,3,2-de>quinolin-8(1H)-one; In methanol; at 20 ℃; for 24h;

DOI:10.1021/ja0365330

Reference yield:

L-tyrosine methyl ester HCl (3417-91-2) → 7-[2-(3-bromo-4-hydroxyphenyl)-1-(triisopropylsilyloxymethyl)ethylamino]-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-pyrrolo[4,3,2-de]quinolin-8-one (613223-70-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 100 percent / triethylamine / dimethylformamide / 3 h / 20 °C

2.1: 65 percent / NBS / dimethylformamide / 2.5 h / 20 °C

3.1: 100 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.75 h / 0 °C

4.1: 90 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

5.1: HCl / methanol / 0.5 h / 20 °C

5.2: 55 percent / methanol / 24 h / 20 °C

With hydrogenchloride; N-Bromosuccinimide; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja0365330

Reference yield:

N-trityl-L-tyrosine methyl ester (18621-06-2) → 7-[2-(3-bromo-4-hydroxyphenyl)-1-(triisopropylsilyloxymethyl)ethylamino]-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-pyrrolo[4,3,2-de]quinolin-8-one (613223-70-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 65 percent / NBS / dimethylformamide / 2.5 h / 20 °C

2.1: 100 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.75 h / 0 °C

3.1: 90 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

4.1: HCl / methanol / 0.5 h / 20 °C

4.2: 55 percent / methanol / 24 h / 20 °C

With hydrogenchloride; N-Bromosuccinimide; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja0365330

upstream raw materials:

7-Methoxy-1-<(4-methylphenyl)sulfonyl>-3,4-dihydropyrrolo<4,3,2-de>quinolin-8(1H)-one

[2-[3-bromo-4-hydroxyphenyl]-1-(triisopropylsilyloxymethyl)ethyl]tritylamine

L-tyrosine methyl ester HCl

N-trityl-L-tyrosine methyl ester