Buchwald–Hartwig amination: 3,5-Dichloropyridazine → tert-butyl N-(5-chloropyridazin-3-yl)carbamate
100% yield, run at 80 °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 | 3,5-Dichloropyridazine | C₄H₂Cl₂N₂ | |
| Reactant | tert-Butyl carbamate | C₅H₁₁NO₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | tert-butyl N-(5-chloropyridazin-3-yl)carbamate | C₉H₁₂ClN₃O₂ | 100% |
Conditions
- Temperature
- 80 °C
Yield
- 100% of tert-butyl N-(5-chloropyridazin-3-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-(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%
- tert-Butyl (5-fluoro-6-methylpyridin-2-yl)carbamate0%
- 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
**_April 15 2016_** 3,5-dichloropyridazine (1 g, 6.71 mmol), tert-butyl carbamate (3.93 g, 33.56 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane) (0.583 g, 1.01 mmol), PdOAc2 (0.452 g, 2.01 mmol) and CS2CO3 (4.37 g, 13.43 mmol) in 1,4-dioxane (20 mL) was degassed through recharged with nitrogen, and was heated at 80 °C overnight. **_April 18 2016_** LCMS showed 23% of the precursor @ 0.55 min (no mass ionization) left on a 2-min basic run. GCMS showed no precursor and 94% of an unknown @ 6.90 min (whihc might be the desired product but not ionizable) on a 10-min run. The reaction was cooled to RT. The crude mixture was concentrated to givr a dark-brown gum. The dark-brown gum was dissolved in EtOAc, washed with water, and evaporated to give a brown solid. The brown soli
The source
This record comes from experimental reaction archive (ord-5053ba4582cb4771951a27c38d53fae2). Open the source and check it against what is on this page.
experimental reaction archive record ord-5053ba4582cb4771951a27c38d53fae2 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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