(R)-3-Bromo-5-(pyrrolidin-2-yl)pyridine

Base Information

• Chemical Name: (R)-3-Bromo-5-(pyrrolidin-2-yl)pyridine
• CAS No.: 83023-56-7
• Molecular Formula: C9H11 Br N2
• Molecular Weight: 227.104
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID40427570
• Mol file: 83023-56-7.mol

Synonyms:83023-56-7;(R)-3-Bromo-5-(pyrrolidin-2-yl)pyridine;(R)-3-Bromo-5-pyrrolidin-2-yl-pyridine;3-bromo-5-[(2R)-pyrrolidin-2-yl]pyridine;(2R)-5-Bromo-3-(2-pyrrolidinyl)pyridine;SCHEMBL18350213;DTXSID40427570;MFCD08063182;BS-53133;CS-0197447;Y11943

Chemical Property of (R)-3-Bromo-5-(pyrrolidin-2-yl)pyridine

Chemical Property:

• PSA: 24.92000
• LogP: 2.59740
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 226.01056
• Heavy Atom Count: 12
• Complexity: 152

Purity/Quality:

97% ^*data from raw suppliers

(R)-3-Bromo-5-pyrrolidin-2-yl-pyridine 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(NC1)C2=CC(=CN=C2)Br
• Isomeric SMILES: C1C[C@@H](NC1)C2=CC(=CN=C2)Br

Technology Process of (R)-3-Bromo-5-(pyrrolidin-2-yl)pyridine

There total 11 articles about (R)-3-Bromo-5-(pyrrolidin-2-yl)pyridine 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: 60.0%

(2'R)-N'-[(1R,2S,5R)-Menthoxycarbonyl]-5-bromonornicotine (263888-13-7) → 3-bromo-5-(pyrrolidin-2-yl)pyridine (83023-56-7)

Guidance literature:

With hydrogenchloride; at 110 ℃; for 60h;

DOI:10.1021/tx990171l

Reference yield:

(E)-N-((5-bromopyridin-3-yl)methylene)-2-methylpropane-2-sulfinamide → 3-bromo-5-(pyrrolidin-2-yl)pyridine (83023-56-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: magnesium; iodine / tetrahydrofuran / 1.25 h / Reflux

1.2: -78 - 20 °C

2.1: hydrogenchloride / methanol / 20 °C

3.1: triethylamine / dichloromethane / 0 - 20 °C

4.1: iodine; benzol / dichloromethane / 20 °C

5.1: sulfuric acid / 4 h / Heating

6.1: sodium tetrahydroborate; ethanol / 2 h / 0 °C

With hydrogenchloride; sodium tetrahydroborate; ethanol; benzol; sulfuric acid; iodine; magnesium; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 4.1: |Hofmann-Loeffler-Freytag Synthesis;

DOI:10.1021/acs.orglett.8b03909

Reference yield:

N-(1-(5-bromopyridin-3-yl)-4-methoxybutyl)-2-methylpropane-2-sulfinamide → 3-bromo-5-(pyrrolidin-2-yl)pyridine (83023-56-7)

Guidance literature:

Multi-step reaction with 5 steps

1: hydrogenchloride / methanol / 20 °C

2: triethylamine / dichloromethane / 0 - 20 °C

3: iodine; benzol / dichloromethane / 20 °C

4: sulfuric acid / 4 h / Heating

5: sodium tetrahydroborate; ethanol / 2 h / 0 °C

With hydrogenchloride; sodium tetrahydroborate; ethanol; benzol; sulfuric acid; iodine; triethylamine; In methanol; dichloromethane; 3: |Hofmann-Loeffler-Freytag Synthesis;

DOI:10.1021/acs.orglett.8b03909

upstream raw materials:

5-Bromo-3-(2-pyrrolidinyl)pyridine

(2'R)-N'-[(1R,2S,5R)-Menthoxycarbonyl]-5-bromonornicotine

ethyl 5-bromo-3-pyridinecarboxylate

3-bromo-5-(4,5-dihydro-3H-pyrrol-2-yl)-pyridine

Downstream raw materials:

(2R)-2-(3-pyridinyl)-1-pyrrolidinebutanoic acid phenylmethyl ester

(+)-nornicotine

Refernces

• 1、 McIntee, Edward J.,Hecht, Stephen S.. "Metabolism of N'-nitrosonornicotine enantiomers by cultured rat esophagus and in vivo in rats". . p. 192 - 199. Retrieved 2007/10/03.