Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

35. Transition Metals

Buchwald-Hartwig Amination Reaction

Organic Chemistry

35. Transition Metals

Buchwald-Hartwig Amination Reaction

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1:14 minutes

Problem 56b

Textbook Question

Suggest reagents to carry out the following transformations. Some may require more than one step.
(b)

Verified step by step guidance

Identify the starting material and the product. The starting material is 2-bromo-3-methylpyridine, and the product is 2-dimethylamino-3-methylpyridine.

Recognize that the transformation involves replacing the bromine atom with a dimethylamino group. This suggests a nucleophilic substitution reaction.

Consider using a nucleophilic substitution reaction such as the Buchwald-Hartwig amination, which is effective for aryl halides. This reaction typically requires a palladium catalyst, a ligand, and a base.

Select appropriate reagents for the Buchwald-Hartwig amination. A common choice is Pd(OAc)₂ as the catalyst, a phosphine ligand like Xantphos, and a base such as sodium tert-butoxide.

Use dimethylamine as the nucleophile in the reaction. The reaction conditions should facilitate the substitution of the bromine atom with the dimethylamino group, yielding the desired product.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Nucleophilic Aromatic Substitution

Nucleophilic aromatic substitution involves the replacement of a leaving group, such as bromine, on an aromatic ring with a nucleophile. This reaction is facilitated by electron-withdrawing groups on the ring, which stabilize the intermediate. In this transformation, the bromine is replaced by an amine group, indicating a nucleophilic substitution process.

Amination

Amination is the process of introducing an amine group into a molecule. In this reaction, the brominated aniline undergoes amination to form a substituted aniline. This typically involves the use of reagents like ammonia or amines, often under conditions that promote nucleophilic attack on the aromatic ring.

Pyridine Ring Chemistry

Pyridine is a basic heterocyclic aromatic organic compound with a nitrogen atom. Its chemistry is influenced by the electron-withdrawing nature of the nitrogen, which affects reactivity and substitution patterns. Understanding pyridine's behavior is crucial for predicting outcomes in reactions involving pyridine derivatives, such as the transformation shown in the image.

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