ethyl 3-(6-(5-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydroisoquinolin-2(1H)-yl)propanoate

Base Information

• Chemical Name: ethyl 3-(6-(5-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydroisoquinolin-2(1H)-yl)propanoate
• CAS No.: 1165924-00-4
• Molecular Formula: C₂₆H₃₀ClN₃O₄
• Molecular Weight: 483.995

Synonyms:ethyl 3-(6-(5-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydroisoquinolin-2(1H)-yl)propanoate

Chemical Property of ethyl 3-(6-(5-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydroisoquinolin-2(1H)-yl)propanoate

Chemical Property:

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Technology Process of ethyl 3-(6-(5-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydroisoquinolin-2(1H)-yl)propanoate

There total 10 articles about ethyl 3-(6-(5-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydroisoquinolin-2(1H)-yl)propanoate 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: 94.0%

5-(3-chloro-4-isopropoxyphenyl)-3-(5-methyl-1,2,3,4-tetrahydroisoquinolin-6-yl)-1,2,4-oxadiazole trifluoroacetate (1165923-46-5) + ethyl acrylate (140-88-5,9003-32-1) → ethyl 3-(6-(5-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydroisoquinolin-2(1H)-yl)propanoate (1165924-00-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 70 ℃; for 0.5h;

DOI:10.1021/ml2000214

Reference yield:

C18H31NO3Si → ethyl 3-(6-(5-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydroisoquinolin-2(1H)-yl)propanoate (1165924-00-4)

Guidance literature:

Multi-step reaction with 8 steps

1: palladium diacetate / acetonitrile / 35 °C

2: tetrabutyl ammonium fluoride / tetrahydrofuran; ethyl acetate / 0.5 h

3: pyridine / dichloromethane / -30 - 20 °C / Inert atmosphere

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 6 h / 100 °C / Inert atmosphere

5: hydroxylamine hydrochloride; sodium hydrogencarbonate / ethanol / 28.5 h / Reflux

6: pyridine / toluene / 2 h / Reflux

7: dichloromethane / 1 h / 0 °C

8: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0.5 h / 70 °C

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; palladium diacetate; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 8: Michael addition;

DOI:10.1021/ml2000214

Reference yield:

1,1-dimethylethyl 6-hydroxy-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate (1165923-89-6) → ethyl 3-(6-(5-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydroisoquinolin-2(1H)-yl)propanoate (1165924-00-4)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / dichloromethane / -30 - 20 °C / Inert atmosphere

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 6 h / 100 °C / Inert atmosphere

3: hydroxylamine hydrochloride; sodium hydrogencarbonate / ethanol / 28.5 h / Reflux

4: pyridine / toluene / 2 h / Reflux

5: dichloromethane / 1 h / 0 °C

6: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0.5 h / 70 °C

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydroxylamine hydrochloride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 6: Michael addition;

DOI:10.1021/ml2000214

upstream raw materials:

5-(3-chloro-4-isopropoxyphenyl)-3-(5-methyl-1,2,3,4-tetrahydroisoquinolin-6-yl)-1,2,4-oxadiazole trifluoroacetate

ethyl acrylate

1,1-dimethylethyl 6-hydroxy-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

1,1-dimethylethyl 5-methyl-6-{[(trifluoromethyl)sulfonyl]oxy}-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Downstream raw materials:

3-(6-(5-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydroisoquinolin-2(1H)-yl)propanoic acid

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