[5-(3-amino-3-methyl-but-1-ynyl)-2-methoxy-phenyl]-[4-(2,4-difluoro-phenylamino)-phenyl]-methanone

Base Information

Chemical Name:[5-(3-amino-3-methyl-but-1-ynyl)-2-methoxy-phenyl]-[4-(2,4-difluoro-phenylamino)-phenyl]-methanone
CAS No.:464190-09-8
Molecular Formula:C₂₅H₂₂F₂N₂O₂
Molecular Weight:420.459
Hs Code.:

Synonyms:[5-(3-amino-3-methyl-but-1-ynyl)-2-methoxy-phenyl]-[4-(2,4-difluoro-phenylamino)-phenyl]-methanone

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Chemical Property of [5-(3-amino-3-methyl-but-1-ynyl)-2-methoxy-phenyl]-[4-(2,4-difluoro-phenylamino)-phenyl]-methanone

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Technology Process of [5-(3-amino-3-methyl-but-1-ynyl)-2-methoxy-phenyl]-[4-(2,4-difluoro-phenylamino)-phenyl]-methanone

There total 6 articles about [5-(3-amino-3-methyl-but-1-ynyl)-2-methoxy-phenyl]-[4-(2,4-difluoro-phenylamino)-phenyl]-methanone 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: 76.0%

: 2978-58-7
1,1-dimethylprop-3-ynylamine

: 464190-38-3
(5-bromo-2-methoxy-phenyl)-[4-(2,4-difluoro-phenylamino)-phenyl]-methanone

: 464190-09-8
[5-(3-amino-3-methyl-but-1-ynyl)-2-methoxy-phenyl]-[4-(2,4-difluoro-phenylamino)-phenyl]-methanone

Guidance literature:: With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine; caesium carbonate; In diethylene glycol dimethyl ether; for 3.5h; Heating;
DOI:10.1016/j.bmcl.2004.03.111

Reference yield:

: 106-37-6
1.4-dibromobenzene

: 464190-09-8
[5-(3-amino-3-methyl-but-1-ynyl)-2-methoxy-phenyl]-[4-(2,4-difluoro-phenylamino)-phenyl]-methanone

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-BuLi / tetrahydrofuran / 0.08 h / -78 °C

1.2: tetrahydrofuran

2.1: CrO₃; H₂SO₄ / acetone / 0.17 h / 20 °C

3.1: 65 percent / Pd(OAc)2; Cs₂CO₃; R-(+)-BINAP / dioxane / 2.5 h / Heating

4.1: 76 percent / CuI; PdCl₂(PPh₃)2; DIPEA / Cs₂CO₃ / bis-(2-methoxy-ethyl) ether / 3.5 h / Heating

With chromium(VI) oxide; bis-triphenylphosphine-palladium(II) chloride; palladium diacetate; copper(l) iodide; n-butyllithium; sulfuric acid; caesium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; caesium carbonate; In tetrahydrofuran; 1,4-dioxane; diethylene glycol dimethyl ether; acetone; 2.1: Jones oxidation / 4.1: Sonogashira coupling;
DOI:10.1016/j.bmcl.2004.03.111

Reference yield:

: 367-25-9,76563-56-9
2,4-difluorophenylamine

: 464190-09-8
[5-(3-amino-3-methyl-but-1-ynyl)-2-methoxy-phenyl]-[4-(2,4-difluoro-phenylamino)-phenyl]-methanone

Guidance literature:: Multi-step reaction with 2 steps

1: 65 percent / Pd(OAc)2; Cs₂CO₃; R-(+)-BINAP / dioxane / 2.5 h / Heating

2: 76 percent / CuI; PdCl₂(PPh₃)2; DIPEA / Cs₂CO₃ / bis-(2-methoxy-ethyl) ether / 3.5 h / Heating

With bis-triphenylphosphine-palladium(II) chloride; palladium diacetate; copper(l) iodide; caesium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; caesium carbonate; In 1,4-dioxane; diethylene glycol dimethyl ether; 2: Sonogashira coupling;
DOI:10.1016/j.bmcl.2004.03.111