3-fluoro-4-((5R)-7-hydroxy-7-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile

Base Information

• Chemical Name: 3-fluoro-4-((5R)-7-hydroxy-7-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile
• CAS No.: 1309475-61-3
• Molecular Formula: C₂₄H₂₂FN₃O₃
• Molecular Weight: 419.455
• Mol file: 1309475-61-3.mol

Synonyms:3-fluoro-4-((5R)-7-hydroxy-7-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile

Chemical Property of 3-fluoro-4-((5R)-7-hydroxy-7-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-fluoro-4-((5R)-7-hydroxy-7-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile

There total 2 articles about 3-fluoro-4-((5R)-7-hydroxy-7-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile 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:

(+)-(R)-4-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-3-fluorobenzonitrile (928134-65-0) → 3-fluoro-4-((5R)-7-hydroxy-7-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile (1309475-61-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tert.-butylhydroperoxide; pyridine / iron(III) chloride / 5 h / Reflux

2.1: tetrahydrofuran / 6 h / -78 - 20 °C / Cooling with acetone-dry ice

2.2: 20 °C

With pyridine; tert.-butylhydroperoxide; iron(III) chloride; In tetrahydrofuran;

Reference yield:

(3-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)magnesium bromide (142402-62-8) + 3-fluoro-4-((R)-7-oxo-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-benzonitrile (1309474-99-4) → 3-fluoro-4-((5R)-7-hydroxy-7-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile (1309475-61-3)

Guidance literature:

(3-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)magnesium bromide; 3-fluoro-4-((R)-7-oxo-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-benzonitrile; In tetrahydrofuran; at -78 - 20 ℃; for 6h; Cooling with acetone-dry ice;

With water; ammonium chloride; In tetrahydrofuran; at 20 ℃;

Reference yield:

3-fluoro-4-((5R)-7-hydroxy-7-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile (1309475-61-3) → 3-fluoro-4-((5R,7S)-7-hydroxy-7-(3-hydroxyphenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile (1309475-62-4)

Guidance literature:

3-fluoro-4-((5R)-7-hydroxy-7-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile; With hydrogenchloride; methanol; In diethyl ether; at 20 ℃; for 2h;

With sodium hydrogencarbonate; In methanol; diethyl ether; water;

upstream raw materials:

(3-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)magnesium bromide

3-fluoro-4-((R)-7-oxo-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-benzonitrile

(+)-(R)-4-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-3-fluorobenzonitrile

Downstream raw materials:

3-fluoro-4-((5R,7S)-7-hydroxy-7-(3-(pyrimidin-2-yl)phenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile

3-fluoro-4-((5R,7S)-7-hydroxy-7-(3-(pyridin-3-yl)phenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile

3-fluoro-4-((5R,7S)-7-hydroxy-7-(3-hydroxyphenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile

3-((5R,7S)-5-(4-cyano-2-fluorophenyl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)phenyl triftuoromethanesulfonate