ethyl 1-{N-[4-(4-methoxyphenyl)but-1-yl]aminoethyl}-2-(3,5-dimethylphenyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-8-carboxylate

Base Information

Chemical Name:ethyl 1-{N-[4-(4-methoxyphenyl)but-1-yl]aminoethyl}-2-(3,5-dimethylphenyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-8-carboxylate
CAS No.:853021-76-8
Molecular Formula:C₃₅H₄₂N₂O₃
Molecular Weight:538.73
Hs Code.:

Synonyms:ethyl 1-{N-[4-(4-methoxyphenyl)but-1-yl]aminoethyl}-2-(3,5-dimethylphenyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-8-carboxylate

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Chemical Property of ethyl 1-{N-[4-(4-methoxyphenyl)but-1-yl]aminoethyl}-2-(3,5-dimethylphenyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-8-carboxylate

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Technology Process of ethyl 1-{N-[4-(4-methoxyphenyl)but-1-yl]aminoethyl}-2-(3,5-dimethylphenyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-8-carboxylate

There total 10 articles about ethyl 1-{N-[4-(4-methoxyphenyl)but-1-yl]aminoethyl}-2-(3,5-dimethylphenyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-8-carboxylate 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: 42.0%

: 853021-75-7
N-[4-(4-methoxyphenyl)but-1-yl]-2-[8-ethoxycarbonyl-2-(3,5-dimethylphenyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl]-2-oxoacetamide

: 853021-76-8
ethyl 1-{N-[4-(4-methoxyphenyl)but-1-yl]aminoethyl}-2-(3,5-dimethylphenyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-8-carboxylate

Guidance literature:: N-[4-(4-methoxyphenyl)but-1-yl]-2-[8-ethoxycarbonyl-2-(3,5-dimethylphenyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl]-2-oxoacetamide; With borane-THF; In tetrahydrofuran; for 3h; Heating;

With 2-(N,N-dimethylamino)ethanol; In methanol; for 3h; Heating;
DOI:10.1016/j.tet.2005.02.041

Reference yield:

: 853021-69-9
ethyl 8-iodo-1,2,3,4-tetrahydroquinoline-6-carboxylate

: 853021-76-8
ethyl 1-{N-[4-(4-methoxyphenyl)but-1-yl]aminoethyl}-2-(3,5-dimethylphenyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-8-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 92 percent / triethylamine; bis(triphenylphosphine)palladium dichloride; copper(I) iodide / 1 h / 0 °C

2.1: 70 percent / palladium dichloride / acetonitrile / 16 h / Heating

3.1: diethyl ether / 1 h / 20 °C

3.2: 95 percent / tetrahydrofuran / 20 °C

4.1: BH₃*THF / tetrahydrofuran / 3 h / Heating

4.2: 42 percent / N,N-dimethylethanolamine / methanol / 3 h / Heating

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; borane-THF; triethylamine; palladium dichloride; In tetrahydrofuran; diethyl ether; acetonitrile; 1.1: Sonogashira coupling;
DOI:10.1016/j.tet.2005.02.041

Reference yield:

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 853021-76-8
ethyl 1-{N-[4-(4-methoxyphenyl)but-1-yl]aminoethyl}-2-(3,5-dimethylphenyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-8-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 60 percent / N-bromosuccinimide / CCl₄ / 3 h / 20 °C

2.1: 60 percent / dimethylformamide / 16 h / Heating

3.1: 95 percent / hydrogen peroxide; NaOH / H₂O / 24 h / Heating

4.1: 60 percent / HCl / H₂O / 72 h / Heating

5.1: 60 percent / iodine monochloride; calcium carbonate / methanol; H₂O / 0 - 20 °C

6.1: 92 percent / triethylamine; bis(triphenylphosphine)palladium dichloride; copper(I) iodide / 1 h / 0 °C

7.1: 70 percent / palladium dichloride / acetonitrile / 16 h / Heating

8.1: diethyl ether / 1 h / 20 °C

8.2: 95 percent / tetrahydrofuran / 20 °C

9.1: BH₃*THF / tetrahydrofuran / 3 h / Heating

9.2: 42 percent / N,N-dimethylethanolamine / methanol / 3 h / Heating

With hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; N-Bromosuccinimide; copper(l) iodide; borane-THF; dihydrogen peroxide; Iodine monochloride; triethylamine; calcium carbonate; palladium dichloride; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; water; N,N-dimethyl-formamide; acetonitrile; 6.1: Sonogashira coupling;
DOI:10.1016/j.tet.2005.02.041