6-bromo-4-<2-(tert-butoxycarbonyl)amino>-5,8-dimethoxyquinoline

Base Information

• Chemical Name: 6-bromo-4-<2-(tert-butoxycarbonyl)amino>-5,8-dimethoxyquinoline
• CAS No.: 133400-98-3
• Molecular Formula: C₂₂H₂₃BrN₂O₄
• Molecular Weight: 459.34
• Mol file: 133400-98-3.mol

Synonyms:6-bromo-4-<2-(tert-butoxycarbonyl)amino>-5,8-dimethoxyquinoline

Chemical Property of 6-bromo-4-<2-(tert-butoxycarbonyl)amino>-5,8-dimethoxyquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-bromo-4-<2-(tert-butoxycarbonyl)amino>-5,8-dimethoxyquinoline

There total 4 articles about 6-bromo-4-<2-(tert-butoxycarbonyl)amino>-5,8-dimethoxyquinoline 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: 64.0%

N-tert-butoxycarbonyl-2-trimethylstannylaniline (114552-32-8) + 6-bromo-5,8-dimethoxy-4-<(trifluoromethanesulfonyl)-oxy>quinoline (133400-92-7) → 6-bromo-5,8-dimethoxy-4-methylquinoline (133400-99-4) + 6-bromo-4-<2-(tert-butoxycarbonyl)amino>-5,8-dimethoxyquinoline (133400-98-3)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride; copper(I) bromide; In 1,4-dioxane; at 90 ℃; for 60h;

DOI:10.1021/jo00011a011

Reference yield:

6-bromo-5,8-dimethoxy-1H-quinolin-4-one (133400-95-0) → 6-bromo-4-<2-(tert-butoxycarbonyl)amino>-5,8-dimethoxyquinoline (133400-98-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / 4-(dimethylamino)pyridine, 2,6-dimethylpyridine / CH₂Cl₂ / 12 h / 23 °C

2: 64 percent / LiCl, Cu(I)Br, tetrakis(triphenylphosphine)palladium / dioxane / 60 h / 90 °C

With 2,6-dimethylpyridine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride; copper(I) bromide; In 1,4-dioxane; dichloromethane;

DOI:10.1021/jo00011a011

Reference yield:

5-{[(2,5-dimethoxyphenylamino)]methylidene}-2,2-dimethyl-4,6-dioxo-1,3-dioxane (97545-51-2) → 6-bromo-4-<2-(tert-butoxycarbonyl)amino>-5,8-dimethoxyquinoline (133400-98-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / Br₂ / acetic acid / 30 h / 23 °C

2: 81 percent / diphenyl ether / 0.33 h / 250 - 260 °C

3: 92 percent / 4-(dimethylamino)pyridine, 2,6-dimethylpyridine / CH₂Cl₂ / 12 h / 23 °C

4: 64 percent / LiCl, Cu(I)Br, tetrakis(triphenylphosphine)palladium / dioxane / 60 h / 90 °C

With 2,6-dimethylpyridine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; bromine; lithium chloride; copper(I) bromide; In 1,4-dioxane; diphenylether; dichloromethane; acetic acid;

DOI:10.1021/jo00011a011

upstream raw materials:

N-tert-butoxycarbonyl-2-trimethylstannylaniline

6-bromo-5,8-dimethoxy-4-<(trifluoromethanesulfonyl)-oxy>quinoline

6-bromo-5,8-dimethoxy-1H-quinolin-4-one

5-{[(2,5-dimethoxyphenylamino)]methylidene}-2,2-dimethyl-4,6-dioxo-1,3-dioxane

Downstream raw materials:

6-bromo-5,8-dimethoxy-4-<2-<(trifluoroacetyl)amino>-phenyl>quinoline

6-bromo-4-<2-<(trifluoroacetyl)amino>-phenyl>quinoline-5,8-dione