methyl 5-amino-4-(2-(benzyloxy)-3,4-dimethoxyphenyl)-3-methyl-6-(5,6,8-trimethoxyquinolin-2-yl)picolinate

Base Information

• Chemical Name: methyl 5-amino-4-(2-(benzyloxy)-3,4-dimethoxyphenyl)-3-methyl-6-(5,6,8-trimethoxyquinolin-2-yl)picolinate
• CAS No.: 1335227-04-7
• Molecular Formula: C₃₅H₃₅N₃O₈
• Molecular Weight: 625.678

Synonyms:methyl 5-amino-4-(2-(benzyloxy)-3,4-dimethoxyphenyl)-3-methyl-6-(5,6,8-trimethoxyquinolin-2-yl)picolinate

Chemical Property of methyl 5-amino-4-(2-(benzyloxy)-3,4-dimethoxyphenyl)-3-methyl-6-(5,6,8-trimethoxyquinolin-2-yl)picolinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-amino-4-(2-(benzyloxy)-3,4-dimethoxyphenyl)-3-methyl-6-(5,6,8-trimethoxyquinolin-2-yl)picolinate

There total 21 articles about methyl 5-amino-4-(2-(benzyloxy)-3,4-dimethoxyphenyl)-3-methyl-6-(5,6,8-trimethoxyquinolin-2-yl)picolinate 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: 74.0%

2-(2-(benzyloxy)-3,4-dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1335227-00-3) + methyl 5-amino-4-bromo-3-methyl-6-(5,6,8-trimethoxyquinolin-2-yl)picolinate (1335227-03-6) → methyl 5-amino-4-(2-(benzyloxy)-3,4-dimethoxyphenyl)-3-methyl-6-(5,6,8-trimethoxyquinolin-2-yl)picolinate (1335227-04-7)

Guidance literature:

With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; water; at 110 ℃; for 16h; Inert atmosphere;

DOI:10.1021/ja207835w

Reference yield:

ethyl 2-(2-(1,3-dioxoisoindolin-2-yl)-N-methoxyacrylamido)-3-methylpent-4-enoate (1335226-95-3) → methyl 5-amino-4-(2-(benzyloxy)-3,4-dimethoxyphenyl)-3-methyl-6-(5,6,8-trimethoxyquinolin-2-yl)picolinate (1335227-04-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: Hoveyda-Grubbs catalyst second generation; p-benzoquinone / toluene / 16 h / 110 °C / Inert atmosphere

2.1: Quinuclidine / methanol / 24 h / 20 °C / Molecular sieve; Inert atmosphere

2.2: 0.5 h / 60 °C / Inert atmosphere

3.1: 2,6-di-tert-butyl-4-methylpyridine / hexafluoropropan-2-ol; dichloromethane / 4 h / -50 - 20 °C / Inert atmosphere

4.1: N-Bromosuccinimide / acetonitrile / 0 - 20 °C / Inert atmosphere

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; hexamethyldistannane / toluene / 16 h / 60 °C / Inert atmosphere

5.2: 16 h / 110 °C / Inert atmosphere

6.1: potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 16 h / 110 °C / Inert atmosphere

With Quinuclidine; potassium phosphate; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Hoveyda-Grubbs catalyst second generation; 2,6-di-tert-butyl-4-methylpyridine; hexamethyldistannane; p-benzoquinone; In 1,4-dioxane; methanol; hexafluoropropan-2-ol; dichloromethane; water; toluene; acetonitrile; 5.1: Stille reaction / 5.2: Stille reaction / 6.1: Suzuki reaction;

DOI:10.1021/ja207835w

Reference yield:

3-ethoxy-N-(2,4,5-trimethoxyphenyl)acrylamide → methyl 5-amino-4-(2-(benzyloxy)-3,4-dimethoxyphenyl)-3-methyl-6-(5,6,8-trimethoxyquinolin-2-yl)picolinate (1335227-04-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sulfuric acid / 0 - 20 °C

2.1: pyridine; trichlorophosphate / N,N-dimethyl-formamide; chlorobenzene / 3 h / Inert atmosphere; Reflux

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; hexamethyldistannane / toluene / 16 h / 60 °C / Inert atmosphere

3.2: 16 h / 110 °C / Inert atmosphere

4.1: potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 16 h / 110 °C / Inert atmosphere

With pyridine; potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; hexamethyldistannane; trichlorophosphate; In 1,4-dioxane; water; N,N-dimethyl-formamide; chlorobenzene; toluene; 3.1: Stille reaction / 3.2: Stille reaction / 4.1: Suzuki reaction;

DOI:10.1021/ja207835w

upstream raw materials:

2-(benzyloxy)-1-bromo-3,4-dimethoxybenzene

2-(2-(benzyloxy)-3,4-dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

methyl 5-amino-4-bromo-3-methyl-6-(5,6,8-trimethoxyquinolin-2-yl)picolinate

ethyl 2-(methoxyamino)-3-methylpent-4-enoate

Downstream raw materials:

(±)-methyl 5-amino-4-(2-(benzyloxy)-5-bromo-3,4-dimethoxyphenyl)-6-(7-bromo-6-methoxy-5,8-dioxo-5,8-dihydroquinolin-2-yl)-3-methylpicolinate

methyl 5-amino-6-(5,8-dihydro-6-methoxy-5,8-dioxo-2-quinolyl)-4-<3,4-dimethoxy-2-(phenylmethoxy)phenyl>-3-methyl-2-pyridinecarboxylate

NSC 45384

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