7-[2-(3-bromo-4-hydroxyphenyl)-1-(tert-butyldimethylsilyloxymethyl)-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-(tert-butyldimethylsilyloxymethyl)-ethylamino]-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-pyrrolo[4,3,2-de]quinolin-8-one
• CAS No.: 425620-72-0
• Molecular Formula: C₃₂H₃₈BrN₃O₅SSi
• Molecular Weight: 684.726
• Mol file: 425620-72-0.mol

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

There total 18 articles about 7-[2-(3-bromo-4-hydroxyphenyl)-1-(tert-butyldimethylsilyloxymethyl)-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: 57.0%

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-(tert-butyldimethylsilyloxymethyl)ethyl]tritylamine (425618-88-8) → 7-[2-(3-bromo-4-hydroxyphenyl)-1-(tert-butyldimethylsilyloxymethyl)-ethylamino]-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-pyrrolo[4,3,2-de]quinolin-8-one (425620-72-0)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 24h;

DOI:10.1039/c1ob05058c

Reference yield:

2-nitroveratraldehyde (55149-84-3) → 7-[2-(3-bromo-4-hydroxyphenyl)-1-(tert-butyldimethylsilyloxymethyl)-ethylamino]-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-pyrrolo[4,3,2-de]quinolin-8-one (425620-72-0)

Guidance literature:

Multi-step reaction with 8 steps

1: potassium hydroxide / ethanol; N,N-dimethyl-formamide / 1.25 h / -2 °C

2: palladium on carbon; formic acid; ammonium formate / methanol / 1 h

3: 2 h / 0 °C

4: lithium aluminium tetrahydride / tetrahydrofuran / 2.5 h / Reflux

5: diphenyl phosphoryl azide; triphenylphosphine; diethylazodicarboxylate / toluene / 9 h

6: potassium tert-butylate / tetrahydrofuran / 6 h / 0 °C

7: 1,1,1,3',3',3'-hexafluoro-propanol; trimethylsilyl trifluoromethanesulfonate; bis-[(trifluoroacetoxy)iodo]benzene / water / 1 h / 0 °C

8: hydrogenchloride / methanol / 24 h / 20 °C

With hydrogenchloride; lithium aluminium tetrahydride; formic acid; 1,1,1,3',3',3'-hexafluoro-propanol; trimethylsilyl trifluoromethanesulfonate; diphenyl phosphoryl azide; palladium on carbon; potassium tert-butylate; ammonium formate; triphenylphosphine; bis-[(trifluoroacetoxy)iodo]benzene; potassium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; toluene; 5: Mitsunobu reaction;

DOI:10.1039/c1ob05058c

Reference yield:

2-Bromo-4-[(S)-3-hydroxy-2-(trityl-amino)-propyl]-phenol (588719-69-1) → 7-[2-(3-bromo-4-hydroxyphenyl)-1-(tert-butyldimethylsilyloxymethyl)-ethylamino]-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-pyrrolo[4,3,2-de]quinolin-8-one (425620-72-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 87 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 2.5 h / 0 °C

2.1: 100 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

3.1: HCl / methanol / 0.5 h / 20 °C

3.2: 54 percent / methanol / 16 h / 20 °C

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

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-(tert-butyldimethylsilyloxymethyl)ethyl]tritylamine

L-tyrosine methyl ester HCl

N-trityl-L-tyrosine methyl ester

Downstream raw materials:

C₂₅H₂₀BrN₃O₄S₂

C₂₆H₂₂BrN₃O₅S

C₃₃H₂₆BrN₃O₆S

C₂₆H₂₁BrN₆O₄S