4-[(2S,3R)-3-(6-bromopyridin-3-yl)-3-hydroxy-2-methylpyrrolidin-1-yl]-2-chlorobenzonitrile

Base Information

Chemical Name:4-[(2S,3R)-3-(6-bromopyridin-3-yl)-3-hydroxy-2-methylpyrrolidin-1-yl]-2-chlorobenzonitrile
CAS No.:1192603-02-3
Molecular Formula:C₁₇H₁₅BrClN₃O
Molecular Weight:392.683
Hs Code.:

Synonyms:4-[(2S,3R)-3-(6-bromopyridin-3-yl)-3-hydroxy-2-methylpyrrolidin-1-yl]-2-chlorobenzonitrile

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Chemical Property of 4-[(2S,3R)-3-(6-bromopyridin-3-yl)-3-hydroxy-2-methylpyrrolidin-1-yl]-2-chlorobenzonitrile

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Technology Process of 4-[(2S,3R)-3-(6-bromopyridin-3-yl)-3-hydroxy-2-methylpyrrolidin-1-yl]-2-chlorobenzonitrile

There total 3 articles about 4-[(2S,3R)-3-(6-bromopyridin-3-yl)-3-hydroxy-2-methylpyrrolidin-1-yl]-2-chlorobenzonitrile 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: 50.0%

: 624-28-2
2,5-dibromopyridine

: 1192608-22-2
2-chloro-4-[(2S)-2-methyl-3-oxopyrrolidin-1-yl]benzonitrile

: 1192603-02-3
4-[(2S,3R)-3-(6-bromopyridin-3-yl)-3-hydroxy-2-methylpyrrolidin-1-yl]-2-chlorobenzonitrile

Guidance literature:: 2,5-dibromopyridine; With n-butyllithium; In diethyl ether; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

2-chloro-4-[(2S)-2-methyl-3-oxopyrrolidin-1-yl]benzonitrile; In tetrahydrofuran; diethyl ether; hexane; at -78 - 20 ℃; regioselective reaction; Inert atmosphere;
DOI:10.1016/j.bmc.2012.11.001

Reference yield:

: 2-chloro-4-[(2S,3S)-3-hydroxy-2-methylpyrrolidin-1-yl]benzonitrile

: 1192603-02-3
4-[(2S,3R)-3-(6-bromopyridin-3-yl)-3-hydroxy-2-methylpyrrolidin-1-yl]-2-chlorobenzonitrile

Guidance literature:: Multi-step reaction with 2 steps

1.1: sulfur trioxide pyridine complex; triethylamine / dimethyl sulfoxide / 1 h / 20 °C

2.1: n-butyllithium / hexane; diethyl ether / 0.5 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

With n-butyllithium; sulfur trioxide pyridine complex; triethylamine; In diethyl ether; hexane; dimethyl sulfoxide;
DOI:10.1016/j.bmc.2012.11.001

Reference yield:

: 60702-69-4
2-chloro-4-fluorobenzonitrile

: 1192603-02-3
4-[(2S,3R)-3-(6-bromopyridin-3-yl)-3-hydroxy-2-methylpyrrolidin-1-yl]-2-chlorobenzonitrile

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium bis(2-methoxyethoxy)aluminum dihydride / toluene; tetrahydrofuran / 3 h / 5 - 70 °C

1.2: 16 h / 20 °C

1.3: 1 h / 100 °C

2.1: sulfur trioxide pyridine complex; triethylamine / dimethyl sulfoxide / 1 h / 20 °C

3.1: n-butyllithium / hexane; diethyl ether / 0.5 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

With n-butyllithium; sodium bis(2-methoxyethoxy)aluminum dihydride; sulfur trioxide pyridine complex; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dimethyl sulfoxide; toluene;
DOI:10.1016/j.bmc.2012.11.001