(1R)-9-fluoro-1-{[4-({2-[(3-fluorophenyl)oxy]ethyl}amino)-1-piperidinyl]methyl}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one

Base Information

• Chemical Name: (1R)-9-fluoro-1-{[4-({2-[(3-fluorophenyl)oxy]ethyl}amino)-1-piperidinyl]methyl}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
• CAS No.: 1073495-64-3
• Molecular Formula: C₂₅H₂₇F₂N₃O₂
• Molecular Weight: 439.505
• Mol file: 1073495-64-3.mol

Synonyms:(1R)-9-fluoro-1-{[4-({2-[(3-fluorophenyl)oxy]ethyl}amino)-1-piperidinyl]methyl}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one

Chemical Property of (1R)-9-fluoro-1-{[4-({2-[(3-fluorophenyl)oxy]ethyl}amino)-1-piperidinyl]methyl}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R)-9-fluoro-1-{[4-({2-[(3-fluorophenyl)oxy]ethyl}amino)-1-piperidinyl]methyl}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one

There total 12 articles about (1R)-9-fluoro-1-{[4-({2-[(3-fluorophenyl)oxy]ethyl}amino)-1-piperidinyl]methyl}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-4-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: 33.0%

[(3-fluorophenyl)oxy]acetaldehyde + (1R)-1-({4-amino-1-piperidinyl}methyl)-9-fluoro-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one (944407-25-4) → (1R)-9-fluoro-1-{[4-({2-[(3-fluorophenyl)oxy]ethyl}amino)-1-piperidinyl]methyl}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one (1073495-64-3)

Guidance literature:

[(3-fluorophenyl)oxy]acetaldehyde; (1R)-1-({4-amino-1-piperidinyl}methyl)-9-fluoro-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one; With sodium sulfate; In methanol; dichloromethane; for 16.5h;

With methanol; sodium tris(acetoxy)borohydride; In dichloromethane; for 5.25h;

Reference yield:

2-(7-fluoro-2-methoxyquinolin-8-yl)acetonitrile (944407-17-4) → (1R)-9-fluoro-1-{[4-({2-[(3-fluorophenyl)oxy]ethyl}amino)-1-piperidinyl]methyl}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one (1073495-64-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: chloro-trimethyl-silane / 2.25 h / 79 °C

2.1: triethylamine / hexanes; acetonitrile / 3 h / 20 °C

3.1: N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate / cyclohexane / 5 h / 86 °C

4.1: N,N,N',N'-tetramethylguanidine / N,N-dimethyl-formamide / 2 h / 50 - 80 °C

5.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / -70 - 10 °C

5.2: 0.5 h

6.1: N-ethyl-N,N-diisopropylamine; Methanesulfonic anhydride / chloroform / 3.5 h / 20 - 65 °C

7.1: hydrogenchloride / water / 0 - 20 °C

8.1: isopropylamine / methanol; acetonitrile / Resolution of racemate

9.1: sodium sulfate / methanol; dichloromethane / 16.5 h

9.2: 5.25 h

With hydrogenchloride; lithium aluminium tetrahydride; chloro-trimethyl-silane; N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; sodium sulfate; isopropylamine; triethylamine; N-ethyl-N,N-diisopropylamine; N,N,N',N'-tetramethylguanidine; Methanesulfonic anhydride; In tetrahydrofuran; methanol; hexanes; dichloromethane; chloroform; cyclohexane; water; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

3-fluorophenoxyacetic acid (404-98-8) → (1R)-9-fluoro-1-{[4-({2-[(3-fluorophenyl)oxy]ethyl}amino)-1-piperidinyl]methyl}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one (1073495-64-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: thionyl chloride / 3 h / 20 °C

2.1: diisobutylaluminium hydride / tetrahydrofuran; dichloromethane; toluene / 3.5 h / -78 °C

3.1: sodium sulfate / methanol; dichloromethane / 16.5 h

3.2: 5.25 h

With thionyl chloride; diisobutylaluminium hydride; sodium sulfate; In tetrahydrofuran; methanol; dichloromethane; toluene;

upstream raw materials:

(1R)-1-({4-amino-1-piperidinyl}methyl)-9-fluoro-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one

7-fluoro-2-methoxy-8-methylquinoline

2-(7-fluoro-2-methoxyquinolin-8-yl)acetonitrile

methyl 2-[7-fluoro-2-(methyloxy)-8-quinolinyl]-2-propenoate