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

Base Information

Chemical Name:(±)-methyl 5-amino-4-(2-(benzyloxy)-5-bromo-3,4-dimethoxyphenyl)-6-(6-methoxy-5,8-dioxo-5,8-dihydroquinolin-2-yl)-3-methylpicolinate
CAS No.:1509897-40-8
Molecular Formula:C₃₃H₂₈BrN₃O₈
Molecular Weight:674.505
Hs Code.:

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

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

There total 22 articles about (±)-methyl 5-amino-4-(2-(benzyloxy)-5-bromo-3,4-dimethoxyphenyl)-6-(6-methoxy-5,8-dioxo-5,8-dihydroquinolin-2-yl)-3-methylpicolinate 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:

: 74615-12-6
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

: 1335227-05-8
(±)-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

: 1509897-40-8
(±)-methyl 5-amino-4-(2-(benzyloxy)-5-bromo-3,4-dimethoxyphenyl)-6-(6-methoxy-5,8-dioxo-5,8-dihydroquinolin-2-yl)-3-methylpicolinate

Guidance literature:: With bromine; In chloroform; at 20 ℃; for 8h; Reagent/catalyst; Darkness; Inert atmosphere;
DOI:10.1021/jo402388f

Reference yield:

: 1335226-95-3
ethyl 2-(2-(1,3-dioxoisoindolin-2-yl)-N-methoxyacrylamido)-3-methylpent-4-enoate

: 1335227-05-8
(±)-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

: 1509897-40-8
(±)-methyl 5-amino-4-(2-(benzyloxy)-5-bromo-3,4-dimethoxyphenyl)-6-(6-methoxy-5,8-dioxo-5,8-dihydroquinolin-2-yl)-3-methylpicolinate

Guidance literature:: Multi-step reaction with 8 steps

1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 48 h / 70 °C / Inert atmosphere; Sealed tube

2: Quinuclidine / methylamine / 60 °C / Inert atmosphere

3: 2,6-di-tert-butyl-4-methylpyridine; 1,1,1,3',3',3'-hexafluoro-propanol / dichloromethane / -50 - 20 °C / Inert atmosphere

4: N-Bromosuccinimide / acetonitrile / 4 h / 0 - 20 °C / Inert atmosphere

5: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; cesium fluoride / toluene / 110 °C / Inert atmosphere

6: potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 110 °C

7: ammonium cerium (IV) nitrate / water; acetonitrile / 0 °C

8: bromine / chloroform / 8 h / 20 °C / Darkness; Inert atmosphere

With Quinuclidine; potassium phosphate; N-Bromosuccinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Hoveyda-Grubbs catalyst second generation; 2,6-di-tert-butyl-4-methylpyridine; ammonium cerium (IV) nitrate; 1,1,1,3',3',3'-hexafluoro-propanol; bromine; cesium fluoride; In 1,4-dioxane; dichloromethane; chloroform; water; toluene; methylamine; acetonitrile; 5: |Stille Cross Coupling / 6: |Suzuki-Miyaura Coupling;
DOI:10.1021/jo402388f

Reference yield:

: 1335227-07-0
2-(benzyloxy)-1-bromo-3,4-dimethoxybenzene

: 1335227-05-8
(±)-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

: 1509897-40-8
(±)-methyl 5-amino-4-(2-(benzyloxy)-5-bromo-3,4-dimethoxyphenyl)-6-(6-methoxy-5,8-dioxo-5,8-dihydroquinolin-2-yl)-3-methylpicolinate

Guidance literature:: Multi-step reaction with 4 steps

1: tert.-butyl lithium / -78 °C / Inert atmosphere

2: potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 110 °C

3: ammonium cerium (IV) nitrate / water; acetonitrile / 0 °C

4: bromine / chloroform / 8 h / 20 °C / Darkness; Inert atmosphere

With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; ammonium cerium (IV) nitrate; bromine; tert.-butyl lithium; In 1,4-dioxane; chloroform; water; acetonitrile; 2: |Suzuki-Miyaura Coupling;
DOI:10.1021/jo402388f