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Buchwald–Hartwig amination: 2,6-Dibromopyridine → 6-Bromo-N-(tetrahydro-2H-pyran-4-yl)pyridin-2-amine

0% yield, as recorded by experimental reaction archive. The written procedure is below.

verified record, 0% yield recorded, Not balanced as written, From experimental reaction archive

Reagents, catalysts and solvents are in the table below.

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The atoms, from reactants to products

BrCCCCCNCCCOCCNBr
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

RoleSpeciesFormulaYield
Reactant2,6-DibromopyridineC₅H₃Br₂N—
Reactant4-AminotetrahydropyranC₅H₁₁NO—
ReagentCesium carbonateCCs₂O₃—
Catalyst1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)C₃₉H₃₂OP₂—
CatalystPalladium (II) acetateC₄H₈O₄Pd—
Solvent1,4-DioxaneC₄H₈O₂—
Product6-Bromo-N-(tetrahydro-2H-pyran-4-yl)pyridin-2-amineC₁₀H₁₃BrN₂O0%

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

This record states no conditions. Temperature, pressure, duration and light are all unrecorded for it, which is a gap in the source rather than a value of zero.

Yield

  • 0% of 6-Bromo-N-(tetrahydro-2H-pyran-4-yl)pyridin-2-amine.

Other recorded runs with the same starting material

No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.

Procedure

Copied from the source record, unedited

to 2,6-dibromopyridine (100 mg, 0.42 mmol), 4-Aminotetrahydropyran (42.7 mg, 0.42 mmol) in dioxane (3 mL) while bubbling N2 was added Xantphos (24.43 mg, 0.04 mmol), CS2CO3 (316 mg, 0.97 mmol) and palladium(II) acetate (9.48 mg, 0.04 mmol). This was heated in a microwave at 130 oC for 30 mins. A small peak corresponding to product was obseved. Discontinued

The source

This record comes from experimental reaction archive (ord-13cef69f8e724020954e5476c0d66794). Open the source and check it against what is on this page.

  • experimental reaction archive record ord-13cef69f8e724020954e5476c0d66794 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.

    experimental record · quality medium · 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.

Where to next

More Buchwald–Hartwig amination records

Other runs of this class, one page per distinct transformation.

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