Buchwald–Hartwig amination, record ord-d5d09a4967464981aba1493aa54fbd9b
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-Bromopyridin-2-yl)methanol | C₆H₆BrNO | |
| Reactant | Morpholine | C₄H₉NO | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | (5-Morpholinopyridin-2-yl)methanol | C₁₀H₁₄N₂O₂ | 19.36% |
Conditions
- Temperature
- 110 °C
Yield
- 19% of (5-Morpholinopyridin-2-yl)methanol.
Procedure
Copied from the source record, unedited
In a 10 mL Microwave vial was (5-bromopyridin-2-yl)methanol (500 mg, 2.66 mmol), morpholine (0.233 mL, 2.66 mmol),cesium carbonate (2166 mg, 6.65 mmol), Pd2(dba)3 (60.9 mg, 0.07 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (115 mg, 0.20 mmol) in dioxane (10 mL) () to give a brown suspension. The reaction mixture was heated to 110 °C for 3h. The reaction mixture was passed over Celite and washed with ethylacetate. The Filtrate was concentrate to dryness to get as a syrupy brown liquid. Water 30ml was added and extracted with ethylacetate (20x 2)ml. THe organic layers are collected, dried over Sodium Sulphate and concentrated to get as a liquid. The crude product was added to a silica gel column and was eluted with ethylacetate 0-70% Pure Collected fractions are evap
The source
This record comes from experimental reaction archive (ord-d5d09a4967464981aba1493aa54fbd9b). Open the source and check it against what is on this page.
experimental reaction archive record ord-d5d09a4967464981aba1493aa54fbd9b 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.