Buchwald–Hartwig amination, record ord-0eb7fc5c164b43bc9a05a46e98a37b12
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 | Iodobenzene | C₆H₅I | |
| Reactant | 4-Methoxy-2-aminobenzothiazole | C₈H₈N₂OS | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | 4-methoxy-N-phenylbenzo[d]thiazol-2-amine | C₁₄H₁₂N₂OS | 15.22% |
Conditions
- Temperature
- 90 °C
Yield
- 15% of 4-methoxy-N-phenylbenzo[d]thiazol-2-amine.
Procedure
Copied from the source record, unedited
4-methoxybenzo[d]thiazol-2-amine (0.216 g, 1.20 mmol), iodobenzene (0.112 mL, 1.00 mmol), XANTPHOS (0.058 g, 0.10 mmol), Pd2(dba)3 (0.027 g, 0.03 mmol) and SODIUM TERT-BUTOXIDE (0.192 g, 2.00 mmol) placed in a sealed reaction via under an atmosphere of nitrogen and heated at 90ºC for 1 hour. LC/MS indicated mainly product, little SM. Cooled, diluted DCM and washed with water and brine. Org phase dried/MgSO4, filtered and evaporated. The crude product was purified by flash silica chromatography, eluting with dichloromethane. Pure fractions were evaporated to dryness to afford 4-methoxy-N- phenylbenzo[d]thiazol-2-amine (0.039 g, 15.22 %) as an colorless solid. EN01327-44-1 (0.039 g, 0.15 mmol, 15.22 %) Not sure why yield so low, crude lc/ms looked fine. Reaction left for several days before
The source
This record comes from experimental reaction archive (ord-0eb7fc5c164b43bc9a05a46e98a37b12). Open the source and check it against what is on this page.
experimental reaction archive record ord-0eb7fc5c164b43bc9a05a46e98a37b12 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.