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Buchwald–Hartwig amination: 2-Bromo-isonicotinic acid methyl ester → methyl 2-(4-fluoro-N-methylanilino)pyridine-4-carboxylate

0% yield, run at 85 °C, 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

COCOCCCNCNCCCCCFCCCBr
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-Bromo-isonicotinic acid methyl esterC₇H₆BrNO₂—
Reactant4-Fluoro-N-methylanilineC₇H₈FN—
ReagentCesium carbonateCCs₂O₃—
Catalyst2-(Dicyclohexylphosphino)biphenylC₂₄H₃₁P—
CatalystBis(dibenzylideneacetone)palladiumC₅₁H₄₂O₃Pd₂—
SolventTolueneC₇H₈—
Productmethyl 2-(4-fluoro-N-methylanilino)pyridine-4-carboxylateC₁₄H₁₃FN₂O₂0%

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
85 °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

  • 0% of methyl 2-(4-fluoro-N-methylanilino)pyridine-4-carboxylate.

Procedure

Copied from the source record, unedited

In a 100 mL round-bottomed flask (t=g) was biphenyl-2-yldicyclohexylphosphine (0.024 g, 0.07 mmol), methyl 2-bromoisonicotinate (.1 g, 0.46 mmol), and 4-fluoro-N-methylaniline (0.070 g, 0.56 mmol) in toluene (3 mL) to give a purple suspension. Pd2dba3 (0.021 g, 0.02 mmol) and CS2CO3 (0.211 g, 0.65 mmol) were added. Flask was placed in an oil bath at 85 °C. LC/MS taken at 1, 2 and 4 hours indicated reaction was not progressing. Reaction was discarded.

The source

This record comes from experimental reaction archive (ord-8fdcadcf8d694b72a4ad9ff8119e3e79). Open the source and check it against what is on this page.

  • experimental reaction archive record ord-8fdcadcf8d694b72a4ad9ff8119e3e79 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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