Buchwald–Hartwig amination: 6-Chloro-3-fluoro-2-methylpyridine → tert-Butyl (5-fluoro-6-methylpyridin-2-yl)carbamate
0% yield, run at 90 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 6-Chloro-3-fluoro-2-methylpyridine | C₆H₅ClFN | |
| Reactant | tert-Butyl carbamate | C₅H₁₁NO₂ | |
| Reagent | Potassium Phosphate, Tribasic | K₃O₄P | |
| 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 | tert-Butyl (5-fluoro-6-methylpyridin-2-yl)carbamate | C₁₁H₁₅FN₂O₂ | 0% |
Conditions
- Temperature
- 90 °C
Yield
- 0% of tert-Butyl (5-fluoro-6-methylpyridin-2-yl)carbamate.
Other recorded runs with the same starting material
No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.
- tert-butyl N-(5-chloropyridazin-3-yl)carbamate100%
- tert-butyl N-(3-fluoro-4-formylphenyl)carbamate97%
- tert-butyl N-(3-fluoro-5-methyl-2-pyridinyl)carbamate26%
- 2-(Tert-butoxycarbonylamino)-6-chloroisonicotinic acid0%
- N-[5-amino-4-methoxy-2-(4-methyl-1-piperazinyl)phenyl]carbamic acid 1,1-dimethylethyl ester0%
- (4-Hydroxymethyl-6-methyl-pyridine-2-yl)-carbamic acid tert-butyl ester0%
- 3-(Boc-amino)pyridinenot recorded
- tert-butyl N-(3-fluoro-5-methyl-2-pyridinyl)carbamate26%
- 3-(Boc-amino)pyridinenot recorded
- 3-(Boc-amino)pyridinenot recorded
- 3-(Boc-amino)pyridinenot recorded
- 3-(Boc-amino)pyridinenot recorded
Procedure
Copied from the source record, unedited
A mixture of 6-chloro-3-fluoro-2-methylpyridine (500 mg, 3.43 mmol), tert- Butyl carbamate (523 mg, 4.47 mmol), Potassium phosphate (1094 mg, 5.15 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (99 mg, 0.17 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (79 mg, 0.09 mmol) were combined in a sealed vial which was purged with nitrogen. Degassed toluene (5 mL) and water (5.00 mL) were added and the mixture was stirred under a nitrogen atmosphere at 90 °C for 6h. The reaction mixture was diluted with EtOAc and washed with saturated NaHCO3 solution, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with mixtures of 5-50%EtOAc in heptane. Many spots isolated, but none of them see
The source
This record comes from experimental reaction archive (ord-849a1d763cb042f7907069ab25fe470c). Open the source and check it against what is on this page.
experimental reaction archive record ord-849a1d763cb042f7907069ab25fe470c 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.
Where to next
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