Buchwald–Hartwig amination: p-Toluidine → 3-Pyridinamine, N-(4-methylphenyl)-

44% yield, run at 60 °C for 16 hours, as recorded by experimental reaction archive. The written procedure is below. One of 863 recorded runs making this product; all of them are compared below.

verified record44% yield recordedNot balanced as writtenFrom experimental reaction archive

Reagents, catalysts and solvents are in the table below.

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The atoms, from reactants to products

Reactants · 1/6

breakingformingbond order changesmapped atom that changes

Drawn from the record's atom map: which bonds break and which form between the reactants and products the source listed. It shows a change in connectivity, not a simulated trajectory and not a mechanism.

What was in the flask

Role	Species	Formula	Yield
Reactant	p-Toluidine	C₇H₉N	—
Reactant	3-Bromopyridine	C₅H₄BrN	—
Reagent	2-tert-Butyl-1,1,3,3-tetramethylguanidine	C₉H₂₁N₃	—
Reagent	5-Methylisoxazole	C₄H₅NO	—
Catalyst	AdBrettPhos	C₅₆H₇₁F₃NO₅PPdS	—
Solvent	Dimethyl Sulfoxide	C₂H₆OS	—
Solvent	Dimethyl Sulfoxide	C₂H₆OS	—
Solvent	Dimethyl Sulfoxide	C₂H₆OS	—
Solvent	Dimethyl Sulfoxide	C₂H₆OS	—
Solvent	Dimethyl Sulfoxide	C₂H₆OS	—
Product	3-Pyridinamine, N-(4-methylphenyl)-	C₁₂H₁₂N₂	43.81%

The equation does not balance as written. That is usual for an experimental record: the source listed what it put in and what it measured, not a stoichiometric equation.

Conditions

Temperature: 60 °C
Duration: 16 hours

Only the dimensions the source stated are listed. Anything absent here was not recorded, and it is not inferred from what the class usually needs.

Yield

44% of 3-Pyridinamine, N-(4-methylphenyl)-.

Every recorded run making this product

863 runs of this class made the same product. The 40 highest-yielding are listed; this page's run is among them.

Reactants	Catalyst	Reagents	Solvent	Temp.	Time	Yield
p-Toluidine; 3-Iodopyridine	t-BuXPhos	MTBD 25	5 × Dimethyl Sulfoxide	60 °C	16 hours	100%
p-Toluidine; 3-Bromopyridine	t-BuXPhos	MTBD 25; Isoxazole, 5-phenyl-	5 × Dimethyl Sulfoxide	60 °C	16 hours	99%
p-Toluidine; 3-Iodopyridine	t-BuXPhos	MTBD 25; Isoxazole, 5-phenyl-	5 × Dimethyl Sulfoxide	60 °C	16 hours	98%
p-Toluidine; 3-Bromopyridine	t-BuXPhos	MTBD 25	5 × Dimethyl Sulfoxide	60 °C	16 hours	98%
p-Toluidine; 3-Iodopyridine	AdBrettPhos	MTBD 25	5 × Dimethyl Sulfoxide	60 °C	16 hours	97%
p-Toluidine; 3-Iodopyridine	t-BuBrettPhos	MTBD 25	5 × Dimethyl Sulfoxide	60 °C	16 hours	96%
p-Toluidine; 3-Bromopyridine	AdBrettPhos	MTBD 25; 3-Phenylisoxazole	5 × Dimethyl Sulfoxide	60 °C	16 hours	95%
p-Toluidine; 3-Bromopyridine	t-BuBrettPhos	MTBD 25	5 × Dimethyl Sulfoxide	60 °C	16 hours	95%
p-Toluidine; 3-Bromopyridine	t-BuXPhos	MTBD 25; 3-Phenylisoxazole	5 × Dimethyl Sulfoxide	60 °C	16 hours	95%
p-Toluidine; 3-Iodopyridine	t-BuXPhos	MTBD 25; 3-Methylisoxazole-5-carboxylic acid ethyl ester	5 × Dimethyl Sulfoxide	60 °C	16 hours	95%
p-Toluidine; 3-Iodopyridine	AdBrettPhos	MTBD 25; 3-Methylisoxazole	5 × Dimethyl Sulfoxide	60 °C	16 hours	95%
p-Toluidine; 3-Iodopyridine	AdBrettPhos	MTBD 25; 3-Methylisoxazole-5-carboxylic acid ethyl ester	5 × Dimethyl Sulfoxide	60 °C	16 hours	95%
p-Toluidine; 3-Bromopyridine	t-BuXPhos	MTBD 25; 4-Phenylisoxazole	5 × Dimethyl Sulfoxide	60 °C	16 hours	94%
p-Toluidine; 3-Bromopyridine	t-BuBrettPhos	MTBD 25; 3-Methylisoxazole	5 × Dimethyl Sulfoxide	60 °C	16 hours	94%
p-Toluidine; 3-Iodopyridine	t-BuBrettPhos	MTBD 25; 3,5-Dimethylisoxazole	5 × Dimethyl Sulfoxide	60 °C	16 hours	94%
p-Toluidine; 3-Bromopyridine	AdBrettPhos	MTBD 25	5 × Dimethyl Sulfoxide	60 °C	16 hours	94%
p-Toluidine; 3-Iodopyridine	t-BuXPhos	MTBD 25; 3-Phenylisoxazole	5 × Dimethyl Sulfoxide	60 °C	16 hours	93%
p-Toluidine; 3-Iodopyridine	t-BuBrettPhos	MTBD 25; 3-Methylisoxazole	5 × Dimethyl Sulfoxide	60 °C	16 hours	93%
p-Toluidine; 3-Iodopyridine	t-BuXPhos	MTBD 25; 4-Phenylisoxazole	5 × Dimethyl Sulfoxide	60 °C	16 hours	93%
p-Toluidine; 3-Iodopyridine	t-BuBrettPhos	MTBD 25; Isoxazole, 5-phenyl-	5 × Dimethyl Sulfoxide	60 °C	16 hours	93%
p-Toluidine; 3-Bromopyridine	t-BuXPhos	MTBD 25; 3-Methylisoxazole	5 × Dimethyl Sulfoxide	60 °C	16 hours	93%
p-Toluidine; 3-Iodopyridine	AdBrettPhos	MTBD 25; Ethyl 5-methylisoxazole-3-carboxylate	5 × Dimethyl Sulfoxide	60 °C	16 hours	93%
p-Toluidine; 3-Bromopyridine	t-BuXPhos	MTBD 25; 3-Methylisoxazole-5-carboxylic acid ethyl ester	5 × Dimethyl Sulfoxide	60 °C	16 hours	93%
p-Toluidine; 3-Iodopyridine	AdBrettPhos	MTBD 25; 3-Phenylisoxazole	5 × Dimethyl Sulfoxide	60 °C	16 hours	92%
p-Toluidine; 3-Iodopyridine	t-BuXPhos	MTBD 25; 3-Methylisoxazole	5 × Dimethyl Sulfoxide	60 °C	16 hours	92%
p-Toluidine; 3-Iodopyridine	t-BuBrettPhos	MTBD 25; 5-Methylisoxazole	5 × Dimethyl Sulfoxide	60 °C	16 hours	92%
p-Toluidine; 3-Iodopyridine	AdBrettPhos	MTBD 25; Isoxazole, 5-phenyl-	5 × Dimethyl Sulfoxide	60 °C	16 hours	92%
p-Toluidine; 3-Iodopyridine	AdBrettPhos	MTBD 25; 3,5-Dimethylisoxazole	5 × Dimethyl Sulfoxide	60 °C	16 hours	92%
p-Toluidine; 3-Iodopyridine	AdBrettPhos	MTBD 25; 5-Methylisoxazole	5 × Dimethyl Sulfoxide	60 °C	16 hours	92%
p-Toluidine; 3-Bromopyridine	AdBrettPhos	MTBD 25; Ethyl 5-methylisoxazole-3-carboxylate	5 × Dimethyl Sulfoxide	60 °C	16 hours	92%
p-Toluidine; 3-Iodopyridine	t-BuXPhos	MTBD 25; Ethyl 5-methylisoxazole-3-carboxylate	5 × Dimethyl Sulfoxide	60 °C	16 hours	91%
p-Toluidine; 3-Iodopyridine	AdBrettPhos	2-tert-Butyl-1,1,3,3-tetramethylguanidine; 3-Methylisoxazole	5 × Dimethyl Sulfoxide	60 °C	16 hours	91%
p-Toluidine; 3-Bromopyridine	AdBrettPhos	MTBD 25; Ethyl 1,2-oxazole-3-carboxylate	5 × Dimethyl Sulfoxide	60 °C	16 hours	90%
p-Toluidine; 3-Bromopyridine	t-BuBrettPhos	MTBD 25; 3-Phenylisoxazole	5 × Dimethyl Sulfoxide	60 °C	16 hours	90%
p-Toluidine; 3-Bromopyridine	t-BuXPhos	MTBD 25; Ethyl 5-methylisoxazole-3-carboxylate	5 × Dimethyl Sulfoxide	60 °C	16 hours	89%
p-Toluidine; 3-Bromopyridine	t-BuBrettPhos	MTBD 25; 3-Methylisoxazole-5-carboxylic acid ethyl ester	5 × Dimethyl Sulfoxide	60 °C	16 hours	89%
p-Toluidine; 3-Iodopyridine	t-BuBrettPhos	MTBD 25; 3-Methylisoxazole-5-carboxylic acid ethyl ester	5 × Dimethyl Sulfoxide	60 °C	16 hours	89%
p-Toluidine; 3-Iodopyridine	t-BuBrettPhos	MTBD 25; 4-Phenylisoxazole	5 × Dimethyl Sulfoxide	60 °C	16 hours	88%
p-Toluidine; 3-Iodopyridine	t-BuBrettPhos	MTBD 25; 3-Phenylisoxazole	5 × Dimethyl Sulfoxide	60 °C	16 hours	88%
p-Toluidine; 3-Iodopyridine	t-BuXPhos	2-tert-Butyl-1,1,3,3-tetramethylguanidine; 3-Phenylisoxazole	5 × Dimethyl Sulfoxide	60 °C	16 hours	88%

Every value is as the source recorded it. A run with no yield was reported without one, and nothing here is averaged, modelled or filled in.

Procedure

Copied from the source record, unedited

These solutions were added to a 384- well source plate (80 µL per well). The Mosquito HTS liquid handling robot was used to dose each of these solutions (200 nL each) into a 1536-well plate.

The source

This record comes from experimental reaction archive (ord-cdd58876c1a64bfbb40e9f07fdf610b9). Open the source and check it against what is on this page.

experimental reaction archive record ord-cdd58876c1a64bfbb40e9f07fdf610b9 from dataset "Ahneman" (doi: 10.1126/science.aar5169). No atom mapping is provided by the source.
experimental record · quality high · source

experimental reaction record.

How to read this record

This is one experiment, not a rule. It says that on one occasion these species were combined under these conditions and this came out. It does not say the reaction will give the same result on your substrate, and nothing on the page has been generalised into a claim that it would.

The pathway is a separate question, kept on separate pages. A mechanism here is the canonical arrow pushing for a class, run on real structures and labelled rule-derived. It is not evidence, and this record is not a mechanism.

Buchwald–Hartwig amination: p-Toluidine → 3-Pyridinamine, N-(4-methylphenyl)-

The atoms, from reactants to products

What was in the flask

Conditions

Yield

Every recorded run making this product

Procedure

The source

How to read this record

Where to next

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