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Buchwald–Hartwig amination: 4-Bromo-2-methoxypyridine → tert-butyl N-[1-(2-methoxy-4-pyridinyl)azetidin-3-yl]carbamate

100% yield, run at 70 °C, as recorded by experimental reaction archive. The written procedure is below.

verified record, 100% 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

COCCCNCCNCOOCCCCCCCNBr
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
Reactant4-Bromo-2-methoxypyridineC₆H₆BrNO—
Reactant3-Aminoazetidine, 3-BOC protectedC₈H₁₆N₂O₂—
Reagentsodium 2-methylpropan-2-olateC₄H₉NaO—
CatalystBinap, (A+-)-C₄₄H₃₂P₂—
CatalystBis(dibenzylideneacetone)palladiumC₅₁H₄₂O₃Pd₂—
SolventTolueneC₇H₈—
Producttert-butyl N-[1-(2-methoxy-4-pyridinyl)azetidin-3-yl]carbamateC₁₄H₂₁N₃O₃100.28%

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
70 °C

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

  • 100% of tert-butyl N-[1-(2-methoxy-4-pyridinyl)azetidin-3-yl]carbamate.

Procedure

Copied from the source record, unedited

A mixture of all the reactants in toluene was heated in a sealed vial at 70 °C overnight. According to LC-MS the reaction was completed and the product had been formed. Toluene was removed, water was added and the product was extracted with DCM. The organic phase was dried through phase separator and concentrated. The crude was used without further purification in the next step, EN01762-02.

The source

This record comes from experimental reaction archive (ord-3870c5bc1f6548e38bd05a0e29b91f59). Open the source and check it against what is on this page.

  • experimental reaction archive record ord-3870c5bc1f6548e38bd05a0e29b91f59 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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