Buchwald–Hartwig amination, record ord-b0d4d24d68264e0ba39e9d5692455d36
One recorded run of this reaction. Below is what the source recorded, and nothing added to it.
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 5-Bromo-2-chloroanisole | C₇H₆BrClO | |
| Reactant | Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylate | C₁₁H₂₀N₂O₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | Tert-butyl 2-(4-chloro-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate | C₁₈H₂₅ClN₂O₃ | 64.57% |
Conditions
- Temperature
- 90 °C
Yield
- 65% of Tert-butyl 2-(4-chloro-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate.
Procedure
Copied from the source record, unedited
A mixture of tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (205 mg, 0.97 mmol), 5-Bromo-2-chloroanisole (235 mg, 1.06 mmol), Sodium tert- butoxide (130 mg, 1.35 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (30.1 mg, 0.05 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (44.2 mg, 0.05 mmol) in toluene (10 mL) under a nitrogen atmosphere was stirred at 90 °C for 12h. The solution was washed with saturated NaHCO3 solution, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude material was loaded on a 24g silica gel column and purified on a Teledyne Isco instrument, eluting with 20% to 40% ethyl acetate in heptane to provide tert-butyl 5-(4-chloro-3-methoxyphenyl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (220 mg, 64.6 %)
The source
This record comes from experimental reaction archive (ord-b0d4d24d68264e0ba39e9d5692455d36). Open the source and check it against what is on this page.
experimental reaction archive record ord-b0d4d24d68264e0ba39e9d5692455d36 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.
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.