Buchwald–Hartwig amination: (2R)-8-chloro-4-methyl-2-phenyl-3,5-dihydro-2H-pyrido[3,2-f][1,4]oxazepine → gamma-Secretase modulator 6
0% yield, run at 120 °C, as recorded by experimental reaction archive. The written procedure is below. One of 3 recorded runs making this product; all of them are compared below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | (2R)-8-chloro-4-methyl-2-phenyl-3,5-dihydro-2H-pyrido[3,2-f][1,4]oxazepine | C₁₅H₁₅ClN₂O | |
| Reactant | 6-Methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-ylamine | C₁₀H₁₂N₄O | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Tris(1,1-dimethylethyl)phosphine | C₁₂H₂₇P | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Product | gamma-Secretase modulator 6 | C₂₅H₂₆N₆O₂ | 0% |
Conditions
- Temperature
- 120 °C
Yield
- 0% of gamma-Secretase modulator 6.
Every recorded run making this product
3 runs of this class made the same product and differed in what else was in the flask. They are listed from the highest yield down, with this page's run marked.
| Catalyst | Reagents | Solvent | Temp. | Time | Yield |
|---|---|---|---|---|---|
| Binap, (A+-)-; Palladium (II) acetate | Potassium Carbonate | Toluene | 120 °C | — | 101% |
| Binap, (A+-)-; Bis(dibenzylideneacetone)palladium | sodium 2-methylpropan-2-olate | Toluene | 100 °C | — | 32% |
| Tris(1,1-dimethylethyl)phosphine; Bis(dibenzylideneacetone)palladium | Cesium carbonate | 120 °C | — | 0% (this run) |
Procedure
Copied from the source record, unedited
Charged a standard microwave vial with a mixture of 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (100 mg, 0.49 mmol), (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (135 mg, 0.49 mmol), cesium carbonate (239 mg, 0.73 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (22.42 mg, 0.02 mmol), Tri-tert- butylphosphonium tetrafluoroborate (14.21 mg, 0.05 mmol), and 1,2-dimethoxyethane. The atmosphere was inerted through vacuum-nitrogen cycles and the contents were heated at 120 °C for a period of 30 min. LCMS indicates reaction progression is less than 10%. Reaction aborted. Not progressed.
The source
This record comes from experimental reaction archive (ord-f55732d796df4a6bad136ec929c58223). Open the source and check it against what is on this page.
experimental reaction archive record ord-f55732d796df4a6bad136ec929c58223 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.
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