methyl 6-(5-(6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinolin-2(1H)-yl)pentyl)-3-hydroxypicolinate

Base Information

• Chemical Name: methyl 6-(5-(6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinolin-2(1H)-yl)pentyl)-3-hydroxypicolinate
• CAS No.: 1310031-64-1
• Molecular Formula: C₂₉H₃₄N₂O₅
• Molecular Weight: 490.599
• Mol file: 1310031-64-1.mol

Synonyms:methyl 6-(5-(6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinolin-2(1H)-yl)pentyl)-3-hydroxypicolinate

Chemical Property of methyl 6-(5-(6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinolin-2(1H)-yl)pentyl)-3-hydroxypicolinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 6-(5-(6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinolin-2(1H)-yl)pentyl)-3-hydroxypicolinate

There total 10 articles about methyl 6-(5-(6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinolin-2(1H)-yl)pentyl)-3-hydroxypicolinate 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:

methyl 3-(benzyloxy)-6-bromopyridine-2-carboxylate (1235142-25-2) → methyl 6-(5-(6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinolin-2(1H)-yl)pentyl)-3-hydroxypicolinate (1310031-64-1)

Guidance literature:

Multi-step reaction with 2 steps

1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere

2: hydrogen; palladium(II) hydroxide / ethyl acetate / 15 h / 20 °C / 760.05 Torr

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; palladium(II) hydroxide; triethylamine; In tetrahydrofuran; ethyl acetate; 1: Sonogashira coupling;

DOI:10.1039/c1cc10787a

Reference yield:

3-hydroxypyridine-2-carboxylic acid (874-24-8) → methyl 6-(5-(6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinolin-2(1H)-yl)pentyl)-3-hydroxypicolinate (1310031-64-1)

Guidance literature:

Multi-step reaction with 5 steps

1: sulfuric acid / 24 h / Reflux

2: bromine / water / 17 h / 0 - 20 °C

3: potassium carbonate / acetone / 15 h / Reflux

4: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere

5: hydrogen; palladium(II) hydroxide / ethyl acetate / 15 h / 20 °C / 760.05 Torr

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; hydrogen; bromine; palladium(II) hydroxide; potassium carbonate; triethylamine; In tetrahydrofuran; water; ethyl acetate; acetone; 4: Sonogashira coupling;

DOI:10.1039/c1cc10787a

Reference yield:

methyl 3-hydroxypicolinate (62733-99-7) → methyl 6-(5-(6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinolin-2(1H)-yl)pentyl)-3-hydroxypicolinate (1310031-64-1)

Guidance literature:

Multi-step reaction with 4 steps

1: bromine / water / 17 h / 0 - 20 °C

2: potassium carbonate / acetone / 15 h / Reflux

3: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere

4: hydrogen; palladium(II) hydroxide / ethyl acetate / 15 h / 20 °C / 760.05 Torr

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; bromine; palladium(II) hydroxide; potassium carbonate; triethylamine; In tetrahydrofuran; water; ethyl acetate; acetone; 3: Sonogashira coupling;

DOI:10.1039/c1cc10787a

upstream raw materials:

3-hydroxypyridine-2-carboxylic acid

methyl 3-hydroxypicolinate

methyl 3-(benzyloxy)-6-bromopyridine-2-carboxylate

2-pent-4-ynyl-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Downstream raw materials:

6-(5-(6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinolin-2(1H)-yl)pentyl)-3-hydroxypicolinaldehyde

6-(5-(6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinolin-2(1H)-yl)pentyl)-3-hydroxypicolinaldehyde oxime