Buchwald–Hartwig amination: 2-Bromo-6-methoxypyridine → 1-[(Z)-1-(4-chlorophenyl)prop-1-enyl]-1-(4-methoxyphenyl)-3-(6-methoxy-2-pyridinyl)-3-methylurea
72% yield, run at 110 °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 | 2-Bromo-6-methoxypyridine | C₆H₆BrNO | |
| Reactant | 1-[(Z)-1-(4-chlorophenyl)prop-1-enyl]-1-(4-methoxyphenyl)-3-methylurea | C₁₈H₁₉ClN₂O₂ | |
| 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 | 1-[(Z)-1-(4-chlorophenyl)prop-1-enyl]-1-(4-methoxyphenyl)-3-(6-methoxy-2-pyridinyl)-3-methylurea | C₂₄H₂₄ClN₃O₃ | 71.95% |
Conditions
- Temperature
- 110 °C
Yield
- 72% of 1-[(Z)-1-(4-chlorophenyl)prop-1-enyl]-1-(4-methoxyphenyl)-3-(6-methoxy-2-pyridinyl)-3-methylurea.
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.
Procedure
Copied from the source record, unedited
(Z)-1-(1-(4-chlorophenyl)prop-1-enyl)-1-(4-methoxyphenyl)-3-methylurea (0.400 g, 1.21 mmol),2-bromo-6-methoxypyridine (0.292 ml, 2.42 mmol),SODIUM TERT- BUTOXIDE (0.349 g, 3.63 mmol),XANTPHOS (0.070 g, 0.12 mmol) and Pd2(dba)3 (0.055 g, 0.06 mmol) were dissolved intoluene (11.80 ml) and sparged under nitrogen for 1 hour. The resulting mixture was then heated to 110 °C for 48 hours or unitil conversion was complete by TLC. NH4Cl (10 mL) was added and the mixture was extracted twice (EtOAc 20 mL). The organic phases were combined, washed with brine (20 mL), dried (MgSO4) and the solvent removed under reduced pressure. The crude product was then purified by flash column chromatography to give (Z)-1-(1-(4-chlorophenyl)prop-1-enyl)-1-(4-methoxyphenyl)-3-(6-methoxypyridin-2-yl)-3-methylurea (0.3
The source
This record comes from experimental reaction archive (ord-055a4c71f284445f89aad15e03c56285). Open the source and check it against what is on this page.
experimental reaction archive record ord-055a4c71f284445f89aad15e03c56285 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
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