Buchwald–Hartwig amination: 2-Bromo-6-methylpyridine → 1-(4-methoxyphenyl)-3-methyl-1-[(Z)-1-(4-methylphenyl)prop-1-enyl]-3-(6-methyl-2-pyridinyl)urea
85% 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-methylpyridine | C₆H₆BrN | |
| Reactant | C/C=C(/c1ccc(C)cc1)N(C(=O)NC)c1ccc(OC)cc1 | C₁₉H₂₂N₂O₂ | |
| 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-(4-methoxyphenyl)-3-methyl-1-[(Z)-1-(4-methylphenyl)prop-1-enyl]-3-(6-methyl-2-pyridinyl)urea | C₂₅H₂₇N₃O₂ | 84.95% |
Conditions
- Temperature
- 110 °C
Yield
- 85% of 1-(4-methoxyphenyl)-3-methyl-1-[(Z)-1-(4-methylphenyl)prop-1-enyl]-3-(6-methyl-2-pyridinyl)urea.
Procedure
Copied from the source record, unedited
(Z)-1-(4-methoxyphenyl)-3-methyl-1-(1-p-tolylprop-1-enyl)urea (0.17200 g, 0.55 mmol),2-bromo-6-methylpyridine (0.126 ml, 1.11 mmol),SODIUM TERT-BUTOXIDE (0.160 g, 1.66 mmol),XANTPHOS (0.032 g, 0.06 mmol) and Pd2(dba)3 (0.025 g, 0.03 mmol) were dissolved intoluene (5.42 ml) and sparged under nitrogen for 15minutes . The resulting mixture was then heated to 110 °C for 29/03/2010 48 hours or unitil conversion was complete by TLC. NH4Cl (10 mL) was added 31-Mar-10 09:49:52 +0100 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-(4-methoxyphenyl)-3-methyl-3-(6-methylpyridin-2-yl)-1-(1-p-tolylp
The source
This record comes from experimental reaction archive (ord-411cbd769b2f48f9a0808a7d2919db15). Open the source and check it against what is on this page.
experimental reaction archive record ord-411cbd769b2f48f9a0808a7d2919db15 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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