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Buchwald–Hartwig amination: 1-(Benzyloxy)-3-bromobenzene → 2-Methyl-1-(3-phenylmethoxyphenyl)-6-(trifluoromethoxy)indole

59% yield, run at 100 °C, as recorded by experimental reaction archive. The written procedure is below.

verified record, 59% 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

CCCCCCCOCFFFCCNCCCCCOCCCCCCCCBr
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
Reactant1-(Benzyloxy)-3-bromobenzeneC₁₃H₁₁BrO—
Reactant2-Methyl-6-(trifluoromethoxy)-1H-indoleC₁₀H₈F₃NO—
Reagentsodium 2-methylpropan-2-olateC₄H₉NaO—
Catalyst2-(Di-tert-butylphosphino)biphenylC₂₀H₂₇P—
CatalystBis(dibenzylideneacetone)palladiumC₅₁H₄₂O₃Pd₂—
SolventTolueneC₇H₈—
Product2-Methyl-1-(3-phenylmethoxyphenyl)-6-(trifluoromethoxy)indoleC₂₃H₁₈F₃NO₂59.07%

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
100 °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

  • 59% of 2-Methyl-1-(3-phenylmethoxyphenyl)-6-(trifluoromethoxy)indole.

Procedure

Copied from the source record, unedited

EN04773-53, _Buchwald coupling, toluene and bromide_ The indole from 4773-25, 1-(benzyloxy)-3-bromobenzene,Pd2(dba)3, JohnPhos and KOtBu were dissolved in toluene. The mixture was warmed at 100 °C for 2h. Ca 60% conversion according to LCMS (product at 2.31 min). This conversion rate seemed faster than for the corresponding aryliodide. Big bacth was performed in 4773-54.

The source

This record comes from experimental reaction archive (ord-0addbbece6dc4ca2acdd8d8c9131d423). Open the source and check it against what is on this page.

  • experimental reaction archive record ord-0addbbece6dc4ca2acdd8d8c9131d423 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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