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Buchwald–Hartwig amination: 2-Bromopyridine → 8-(2-Pyridinyl)-1,4-dioxa-8-azaspiro[4.5]decane

67% yield, as recorded by experimental reaction archive. The written procedure is below.

verified record, 67% 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

CCCCNCCCCCOCCONCBr
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-BromopyridineC₅H₄BrN—
Reactant1,4-Dioxa-8-azaspiro(4.5)decaneC₇H₁₃NO₂—
Reagentsodium 2-methylpropan-2-olateC₄H₉NaO—
Catalyst2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylC₃₃H₄₉P—
CatalystPalladium (II) acetateC₄H₈O₄Pd—
Product8-(2-Pyridinyl)-1,4-dioxa-8-azaspiro[4.5]decaneC₁₂H₁₆N₂O₂66.56%

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

  • 67% of 8-(2-Pyridinyl)-1,4-dioxa-8-azaspiro[4.5]decane.

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

The same procrdure as EN03653-93-01.

The source

This record comes from experimental reaction archive (ord-00b95f6f20354bb6923efd18c2b3c116). Open the source and check it against what is on this page.

  • experimental reaction archive record ord-00b95f6f20354bb6923efd18c2b3c116 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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The atom map, the bonds that break and form, and records running the same transformation.

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