dimethyl 5,5'-(6,6'-(buta-1,3-diyne-1,4-diyl)bis(3-tert-butyl-6,1-phenylene)bis(ethyne-2,1-diyl))dipicolinate

Base Information

Chemical Name:dimethyl 5,5'-(6,6'-(buta-1,3-diyne-1,4-diyl)bis(3-tert-butyl-6,1-phenylene)bis(ethyne-2,1-diyl))dipicolinate
CAS No.:1350553-54-6
Molecular Formula:C₄₂H₃₆N₂O₄
Molecular Weight:632.759
Hs Code.:

Synonyms:dimethyl 5,5'-(6,6'-(buta-1,3-diyne-1,4-diyl)bis(3-tert-butyl-6,1-phenylene)bis(ethyne-2,1-diyl))dipicolinate

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Chemical Property of dimethyl 5,5'-(6,6'-(buta-1,3-diyne-1,4-diyl)bis(3-tert-butyl-6,1-phenylene)bis(ethyne-2,1-diyl))dipicolinate

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Technology Process of dimethyl 5,5'-(6,6'-(buta-1,3-diyne-1,4-diyl)bis(3-tert-butyl-6,1-phenylene)bis(ethyne-2,1-diyl))dipicolinate

There total 6 articles about dimethyl 5,5'-(6,6'-(buta-1,3-diyne-1,4-diyl)bis(3-tert-butyl-6,1-phenylene)bis(ethyne-2,1-diyl))dipicolinate 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%

: 1350553-51-3
methyl 5-((5-tert-butyl-2-ethynylphenyl)ethynyl)picolinate

: 1350553-54-6
dimethyl 5,5'-(6,6'-(buta-1,3-diyne-1,4-diyl)bis(3-tert-butyl-6,1-phenylene)bis(ethyne-2,1-diyl))dipicolinate

Guidance literature:: With pyridine; trans-bis(triphenylphosphine)palladium dichloride; iodine; copper diacetate; diisopropylamine; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1016/j.jorganchem.2011.07.007

Reference yield:

: 29682-15-3
methyl 5-bromopicolinate

: 1350553-54-6
dimethyl 5,5'-(6,6'-(buta-1,3-diyne-1,4-diyl)bis(3-tert-butyl-6,1-phenylene)bis(ethyne-2,1-diyl))dipicolinate

Guidance literature:: Multi-step reaction with 6 steps

1: copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine / tetrahydrofuran / 18 h / 60 °C / Inert atmosphere

2: potassium fluoride / methanol; dichloromethane / 2 h / 20 °C

3: copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

4: copper(l) iodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; diisopropylamine / N,N-dimethyl-formamide / 48 h / 70 °C / Inert atmosphere

5: tetrabutyl ammonium fluoride / tetrahydrofuran; water / 3 h / 20 °C

6: pyridine; trans-bis(triphenylphosphine)palladium dichloride; iodine; copper diacetate; diisopropylamine / tetrahydrofuran / 2 h / 20 °C

With pyridine; potassium fluoride; copper(l) iodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; trans-bis(triphenylphosphine)palladium dichloride; tetrabutyl ammonium fluoride; iodine; copper diacetate; triethylamine; diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 1: Sonogashira-Hagihara reaction / 3: Sonogashira-Hagihara reaction;
DOI:10.1016/j.jorganchem.2011.07.007

Reference yield:

: 1350553-45-5
methyl 5-((5-tert-butyl-2-(trifluoromethylsulfonyloxy)phenyl)ethynyl)picolinate

: 1350553-54-6
dimethyl 5,5'-(6,6'-(buta-1,3-diyne-1,4-diyl)bis(3-tert-butyl-6,1-phenylene)bis(ethyne-2,1-diyl))dipicolinate

Guidance literature:: Multi-step reaction with 3 steps

1: copper(l) iodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; diisopropylamine / N,N-dimethyl-formamide / 48 h / 70 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride / tetrahydrofuran; water / 3 h / 20 °C

3: pyridine; trans-bis(triphenylphosphine)palladium dichloride; iodine; copper diacetate; diisopropylamine / tetrahydrofuran / 2 h / 20 °C

With pyridine; copper(l) iodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; trans-bis(triphenylphosphine)palladium dichloride; tetrabutyl ammonium fluoride; iodine; copper diacetate; diisopropylamine; In tetrahydrofuran; water; N,N-dimethyl-formamide;
DOI:10.1016/j.jorganchem.2011.07.007