tert-butyl {[6-(5-cyanopent-1-yn-1-yl)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate

Base Information

Chemical Name:tert-butyl {[6-(5-cyanopent-1-yn-1-yl)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate
CAS No.:660451-99-0
Molecular Formula:C₃₂H₃₇N₃O₂
Molecular Weight:495.665
Hs Code.:

Synonyms:tert-butyl {[6-(5-cyanopent-1-yn-1-yl)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate

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Chemical Property of tert-butyl {[6-(5-cyanopent-1-yn-1-yl)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate

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Technology Process of tert-butyl {[6-(5-cyanopent-1-yn-1-yl)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate

There total 11 articles about tert-butyl {[6-(5-cyanopent-1-yn-1-yl)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate 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: 84.0%

: 660449-16-1
3-{[(tert-butoxycarbonyl)amino]methyl}-4-(4-methylphenyl)-2-(2-methylpropyl)quinolin-6-yl trifluoromethanesulfonate

: 14918-21-9
5-hexynonitrile

: 660451-99-0
tert-butyl {[6-(5-cyanopent-1-yn-1-yl)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate

Guidance literature:: With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; at 80 ℃; for 0.166667h;

Reference yield:

: 304854-54-4
2-amino-5-bromo-N-methoxy-N-methyl-benzamide

: 660451-99-0
tert-butyl {[6-(5-cyanopent-1-yn-1-yl)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate

Guidance literature:: Multi-step reaction with 8 steps

1.1: tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

2.1: methanesulfonic acid / toluene / 17 h / Reflux

3.1: palladium diacetate; 2,2'-bis(diphenylphosphino)biphenyl / tert-butyl alcohol / 15 h / 70 °C / Inert atmosphere

4.1: trifluoroacetic acid / tetrahydrofuran / 4 h / 20 °C

5.1: ammonia; hydrogen / tetrahydrofuran; methanol / 8 h / 70 °C / 3750.38 Torr

6.1: tetrahydrofuran / 3 h / 20 °C

7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C

7.2: 0.5 h / 20 °C

8.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 0.17 h / 80 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; methanesulfonic acid; ammonia; hydrogen; palladium diacetate; sodium hydride; 2,2'-bis(diphenylphosphino)biphenyl; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide; toluene; mineral oil; tert-butyl alcohol; 8.1: Sonogashira coupling;
DOI:10.1021/jm101236h

Reference yield:

: 1262394-32-0
6-tert-butoxy-4-(4-methylphenyl)-2-(2-methylpropyl)quinoline-3-carbonitrile

: 660451-99-0
tert-butyl {[6-(5-cyanopent-1-yn-1-yl)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate

Guidance literature:: Multi-step reaction with 5 steps

1.1: trifluoroacetic acid / tetrahydrofuran / 4 h / 20 °C

2.1: ammonia; hydrogen / tetrahydrofuran; methanol / 8 h / 70 °C / 3750.38 Torr

3.1: tetrahydrofuran / 3 h / 20 °C

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C

4.2: 0.5 h / 20 °C

5.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 0.17 h / 80 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; ammonia; hydrogen; sodium hydride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; mineral oil; 5.1: Sonogashira coupling;
DOI:10.1021/jm101236h