methyl 4-(benzyloxy)-3,7,8,9-tetrahydro-8-methanesulfonyloxy-6-(methoxycarbonyl)-6H-pyrrolo[3,2-f]quinoline-2-carboxylate

Base Information

Chemical Name:methyl 4-(benzyloxy)-3,7,8,9-tetrahydro-8-methanesulfonyloxy-6-(methoxycarbonyl)-6H-pyrrolo[3,2-f]quinoline-2-carboxylate
CAS No.:757951-86-3
Molecular Formula:C₂₃H₂₄N₂O₈S
Molecular Weight:488.518
Hs Code.:

Synonyms:methyl 4-(benzyloxy)-3,7,8,9-tetrahydro-8-methanesulfonyloxy-6-(methoxycarbonyl)-6H-pyrrolo[3,2-f]quinoline-2-carboxylate

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Chemical Property of methyl 4-(benzyloxy)-3,7,8,9-tetrahydro-8-methanesulfonyloxy-6-(methoxycarbonyl)-6H-pyrrolo[3,2-f]quinoline-2-carboxylate

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Technology Process of methyl 4-(benzyloxy)-3,7,8,9-tetrahydro-8-methanesulfonyloxy-6-(methoxycarbonyl)-6H-pyrrolo[3,2-f]quinoline-2-carboxylate

There total 16 articles about methyl 4-(benzyloxy)-3,7,8,9-tetrahydro-8-methanesulfonyloxy-6-(methoxycarbonyl)-6H-pyrrolo[3,2-f]quinoline-2-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: 75.0%

: 124-63-0
methanesulfonyl chloride

: 174868-40-7
methyl 4-(benzyloxy)-3,7,8,9-tetrahydro-8-hydroxy-6-(methoxycarbonyl)-6H-pyrrolo[3,2-f]quinoline-2-carboxylate

: 757951-86-3
methyl 4-(benzyloxy)-3,7,8,9-tetrahydro-8-methanesulfonyloxy-6-(methoxycarbonyl)-6H-pyrrolo[3,2-f]quinoline-2-carboxylate

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1021/ol0489548

Reference yield:

: 25945-96-4
2-benzyloxy-4-nitro-phenylamine

: 757951-86-3
methyl 4-(benzyloxy)-3,7,8,9-tetrahydro-8-methanesulfonyloxy-6-(methoxycarbonyl)-6H-pyrrolo[3,2-f]quinoline-2-carboxylate

Guidance literature:: Multi-step reaction with 14 steps

1.1: 91 percent / ICI / tetrahydrofuran / 3 h / Heating

2.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

2.2: tetrahydrofuran / 12 h / 20 °C

3.1: 0.91 g / TBAF / tetrahydrofuran / 48 h / 20 °C

4.1: 56 percent / iPr₂NEt; ZnBr₂ / Pd(PPh₃)4 / tetrahydrofuran / 11 h / Heating

5.1: H₂ / PtO₂ / ethyl acetate / 12 h / 20 °C

6.1: NIS / tetrahydrofuran / 0.08 h / 0 °C

7.1: 247 mg / DMAP / pyridine / 2.5 h / 0 °C

8.1: 83 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / dimethylformamide / 2 h / 50 °C

9.1: quinoline; H₂ / Pd/C / tetrahydrofuran; methanol / 8 h / 20 °C

10.1: diethyl azodicarboxylate; PPh₃ / tetrahydrofuran; toluene / 2 h / 20 °C

11.1: 400 mg / K₂CO₃ / methanol / 12 h / 20 °C

12.1: MCPBA / CH₂Cl₂ / 0.08 h / 0 °C

13.1: 20.1 mg / Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 0.17 h / 0 °C

14.1: 75 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

With quinoline; triethylsilane; dmap; N-iodo-succinimide; copper(l) iodide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; potassium carbonate; steareth-10; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; zinc dibromide; diethylazodicarboxylate; platinum(IV) oxide; bis-triphenylphosphine-palladium(II) chloride; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; pyridine; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; 4.1: Negishi coupling / 8.1: Sonogashira reaction / 10.1: intramolecular Mitsunobu reaction;
DOI:10.1021/ol0489548

Reference yield:

: 100-39-0
benzyl bromide

: 757951-86-3
methyl 4-(benzyloxy)-3,7,8,9-tetrahydro-8-methanesulfonyloxy-6-(methoxycarbonyl)-6H-pyrrolo[3,2-f]quinoline-2-carboxylate

Guidance literature:: Multi-step reaction with 15 steps

1.1: 93 percent / K₂CO₃ / acetone / 8 h / Heating

2.1: 91 percent / ICI / tetrahydrofuran / 3 h / Heating

3.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

3.2: tetrahydrofuran / 12 h / 20 °C

4.1: 0.91 g / TBAF / tetrahydrofuran / 48 h / 20 °C

5.1: 56 percent / iPr₂NEt; ZnBr₂ / Pd(PPh₃)4 / tetrahydrofuran / 11 h / Heating

6.1: H₂ / PtO₂ / ethyl acetate / 12 h / 20 °C

7.1: NIS / tetrahydrofuran / 0.08 h / 0 °C

8.1: 247 mg / DMAP / pyridine / 2.5 h / 0 °C

9.1: 83 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / dimethylformamide / 2 h / 50 °C

10.1: quinoline; H₂ / Pd/C / tetrahydrofuran; methanol / 8 h / 20 °C

11.1: diethyl azodicarboxylate; PPh₃ / tetrahydrofuran; toluene / 2 h / 20 °C

12.1: 400 mg / K₂CO₃ / methanol / 12 h / 20 °C

13.1: MCPBA / CH₂Cl₂ / 0.08 h / 0 °C

14.1: 20.1 mg / Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 0.17 h / 0 °C

15.1: 75 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

With quinoline; triethylsilane; dmap; N-iodo-succinimide; copper(l) iodide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; potassium carbonate; steareth-10; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; zinc dibromide; diethylazodicarboxylate; platinum(IV) oxide; bis-triphenylphosphine-palladium(II) chloride; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; pyridine; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; 5.1: Negishi coupling / 9.1: Sonogashira reaction / 11.1: intramolecular Mitsunobu reaction;
DOI:10.1021/ol0489548