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Apr 25, 2023 109 likes •300 views

Developing Methods for Regioselective Iodination of Heterocycles in Mild Conditions Christopher Bilham Santa Barbara City College Chemical Engineering Mentor: Lindsay Smith Faculty Advisor:

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Developing Methods for Regioselective Iodination of Heterocycles in Mild Conditions Christopher Bilham Santa Barbara City College Chemical Engineering

Mentor: Lindsay Smith Faculty Advisor: Armen Zakarian

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Synthesizing a Better Future

Big Picture

Develop methods for effective iodination of a class of

compounds known as heterocycles

Low Cost/High Yield
Synthetically useful
Applications
Pharmaceuticals
Materials
Agrochemicals
Organic Synthesis
Mild Conditions
Regioselective

Lipitor By Pfizer

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Project Goals Summer 2013

 Substrates – ‘Starting Material’  Screen these substrates under different conditions

2 – Methoxypyridine Dibenzofuran N-Methylpyrrole

GOAL: Screen all substrates and develop a comprehensive understanding of the reaction methods and their effectiveness

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Methods

 Reaction Setup  Isolation – Column Chromatography

 Monitor by Thin Layer Chromatography  Characterization by H-NMR

Inlet Adapter Reaction Flask Stir Plate Silica Column Collection Tubes 600 MHz NMR Spectrometer Silica Plate Spots Potassium Permanganate Stained

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Reagents
TriFluoroacetic Acid (TFA)
N-IodoSuccinimide (NIS)
TetraHydroFuran (THF)

Screening Results

 N-Methylpyrrole

NOTE: Product hard to isolate due to volatility Trace Amounts 1. TFA

2. NIS
3. THF
40° C, 30 min

97% 100% Conversion

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Reagents
N-IodoSuccinimide (NIS)
HexaFluoro-2-propanol (HFIP)

Screening Results

 N-Methylpyrrole

NOTES: Thin Layer Chromatography

showed formation of product at room temp after 30 minutes but no product was isolated in the morning.

1. NIS

2. HFIP

R.T, Overnight Unknown Conversion

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Reagents
TriFluoroacetic Acid (TFA)
N-IodoSuccinimide (NIS)

Screening Results

 N-Methylpyrrole

NOTE: Started at 0 ° C brought to reflux NO RXN NO RXN 1. NIS

2. TFA

Reflux, Overnight

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Reagents
N-IodoSuccinimide (NIS)
HexaFluoro-2-Propanol (HFIP)

Screening Results

 Dibenzofuran

1. NIS

2. HFIP

R.T, Overnight 64.5% Conversion

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Reagents
N-IodoSuccinimide (NIS)
TriFluoroacetic Acid (TFA)

Screening Results

 Dibenzofuran

NOTE: Solution solidified at 15 min 1. NIS

2. TFA

50 ° C, 15 min 84% 4.0% 88% Conversion

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Reagents
TriFluoroacetic Acid (TFA)
N-IodoSuccinimide (NIS)
TetraHydroFuran (THF)

Screening Results

 Dibenzofuran

NO RXN NO RXN 1. TFA

2. THF
3. NIS

50 °C, Overnight NOTE: Started at 0 ° C brought to 50 ° C

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97%

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Accomplishments

Skills – Organic Chemistry Lab Work

Run a quality reaction from start to end
Identify products
Isolate products

Presentation and Communication

Power Point Presentations
Public Speaking Practice
Conveying Scientific Information

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Now what?

Simple! Screen More Substrates!

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Acknowledgements

Mentor: Lindsay Smith Faculty Advisor: Armen Zakarian

The Zakarian Group

Dr. Armen Zakarian
Lindsay Smith
Aaron Herrmann

INSET

Dr. Jens-Uwe Kuhn
Dr. Maria Napoli
Dr. Nick Arnold
Assisting Faculty

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General Equipment Questions

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