9-benzhydryloxy-5-(2,6-difluoro-phenyl)-7-(4-fluoro-benzyl)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one

Base Information

• Chemical Name: 9-benzhydryloxy-5-(2,6-difluoro-phenyl)-7-(4-fluoro-benzyl)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one
• CAS No.: 684287-35-2
• Molecular Formula: C₃₇H₂₅F₃N₂O₂
• Molecular Weight: 586.613
• Mol file: 684287-35-2.mol

Synonyms:9-benzhydryloxy-5-(2,6-difluoro-phenyl)-7-(4-fluoro-benzyl)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one

Chemical Property of 9-benzhydryloxy-5-(2,6-difluoro-phenyl)-7-(4-fluoro-benzyl)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-benzhydryloxy-5-(2,6-difluoro-phenyl)-7-(4-fluoro-benzyl)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one

There total 9 articles about 9-benzhydryloxy-5-(2,6-difluoro-phenyl)-7-(4-fluoro-benzyl)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one 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: 17.0%

trifluoro-methanesulfonic acid 9-benzhydryloxy-7-(4-fluoro-benzyl)-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl ester (684284-68-2) + 2,6-difluorophenylboronic acid (162101-25-9) → 9-benzhydryloxy-7-(4-fluoro-benzyl)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one (684287-36-3) + 9-benzhydryloxy-5-(2,6-difluoro-phenyl)-7-(4-fluoro-benzyl)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one (684287-35-2)

Guidance literature:

With potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In ethanol; water; toluene; at 120 ℃; for 3h;

Reference yield:

trifluoro-methanesulfonic acid 9-benzhydryloxy-7-(4-fluoro-benzyl)-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl ester (684284-68-2) + 2,6-difluorophenylboronic acid (162101-25-9) → 9-benzhydryloxy-5-(2,6-difluoro-phenyl)-7-(4-fluoro-benzyl)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one (684287-35-2)

Guidance literature:

With potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In ethanol; toluene; at 120 ℃; for 3h;

DOI:10.1016/j.bmcl.2006.05.016

Reference yield:

7-(4-fluoro-benzyl)-5,9-dihydroxy-pyrrolo[3,4-g]quinoline-6,8-dione (684284-29-5) → 9-benzhydryloxy-5-(2,6-difluoro-phenyl)-7-(4-fluoro-benzyl)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one (684287-35-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 63 percent / NaOH / dioxane; H₂O / 1 h / 20 °C

2.1: 80 percent / 1,2-dichloro-ethane / 3 h / 70 °C

3.1: 100 percent / K₂CO₃; 4-dimethylaminopyridine / tetrahydrofuran; H₂O / 12 h / 20 °C

4.1: 82 percent / DEAD; Ph₃P / CH₂Cl₂ / 3 h / 20 °C

5.1: aq. LiBH₄ / tetrahydrofuran / 0 - 20 °C

5.2: Ac₂O; DMAP / CH₂Cl₂ / 12 h / 20 °C

5.3: 47 percent / triethylsilane; TMSOTf; 2,6-lutidine / 12 h / 20 °C

6.1: 100 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

7.1: 43 percent / Cs₂CO₃ / CH₂Cl₂ / 1 h / Heating

8.1: aq. K₂CO₃ / tetrakis-(triphenylphosphine)-palladium⁽⁰⁾ / toluene; ethanol / 3 h / 120 °C

With dmap; sodium hydroxide; lithium borohydride; tetrabutyl ammonium fluoride; potassium carbonate; caesium carbonate; triphenylphosphine; diethylazodicarboxylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; 1,2-dichloro-ethane; toluene;

DOI:10.1016/j.bmcl.2006.05.016

upstream raw materials:

trifluoro-methanesulfonic acid 9-benzhydryloxy-7-(4-fluoro-benzyl)-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl ester

2,6-difluorophenylboronic acid

7-(4-fluoro-benzyl)-5,9-dihydroxy-pyrrolo[3,4-g]quinoline-6,8-dione

carbonic acid ethyl ester 7-(4-fluoro-benzyl)-9-hydroxy-6,8-dioxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl ester

Downstream raw materials:

5-(2,6-difluoro-phenyl)-7-(4-fluoro-benzyl)-9-hydroxy-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one trifluoroacetate