Buchwald–Hartwig amination, record ord-c0d27ca6d70a4e629ed6ea0a3371d1c9
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 | 6-Bromo-1H-indazole | C₇H₅BrN₂ | |
| Reactant | Pyrrolidine | C₄H₉N | |
| Reagent | lithium bis(trimethylsilyl)azanide | C₆H₁₈LiNSi₂ | |
| Catalyst | 2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl | C₃₀H₄₃O₂P | |
| Catalyst | Chloro[2-(dicyclohexylphosphino)-2 inverted exclamation mark,6 inverted exclamation mark-diisopropoxybiphenyl][2-(2-aminoethyl)phenyl]palladium(II) | C₃₈H₅₃ClNO₂PPd | |
| Solvent | Tetrahydrofuran | C₄H₈O | |
| Product | 1h-Indazole,6-(1-pyrrolidinyl)- | C₁₁H₁₃N₃ | 93.74% |
Conditions
- Temperature
- 60 °C
Yield
- 94% of 1h-Indazole,6-(1-pyrrolidinyl)-.
Procedure
Copied from the source record, unedited
_This reaction is done in triplicate_ : 6-bromo-1H-indazole (1.2 g, 6.09 mmol, 1 eq each), chloro(2-dicyclohexylphosphino-2',6'-di-i- propoxy-1,1'-biphenyl)[2-(2-aminoethylphenyl)]palladium(II), methyl-t- butylether adduct (RuPhos-PreCatalyst) (89 mg, 0.12 mmol, 0.02 eq each), 2-Dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl (RuPhos ligand) (57 mg, 0.12 mmol, 0.02 eq, each) were taken a stoppered bottle, flush with N2, pyrrolidine (0.60 ml, 522 mg. 7.34 mmol, 1.2 eq, each) and lithium bis(trimethylsilyl)amide (1M soln in THF, 15 ml, 15 mmol, 2.46 eq, each) were added in succession, flushed with N2, stoppered the bottle and stirred at 60 °C. LC-MS, after 2 hrs, showed that all the starting material is consumed. Cooled to r.t, queched the reaction with 2M HCl (9 ml, each), combined
The source
This record comes from experimental reaction archive (ord-c0d27ca6d70a4e629ed6ea0a3371d1c9). Open the source and check it against what is on this page.
experimental reaction archive record ord-c0d27ca6d70a4e629ed6ea0a3371d1c9 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.