Buchwald–Hartwig amination: 2-Bromo-3-methylpyridine → tert-butyl (3R)-3-[(3-methylpyridin-2-yl)amino]piperidine-1-carboxylate
70% yield, run at 115 °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-3-methylpyridine | C₆H₆BrN | |
| Reactant | tert-butyl (3R)-3-aminopiperidine-1-carboxylate | C₁₀H₂₀N₂O₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | tert-butyl (3R)-3-[(3-methylpyridin-2-yl)amino]piperidine-1-carboxylate | C₁₆H₂₅N₃O₂ | 69.75% |
Conditions
- Temperature
- 115 °C
Yield
- 70% of tert-butyl (3R)-3-[(3-methylpyridin-2-yl)amino]piperidine-1-carboxylate.
Procedure
Copied from the source record, unedited
Production using the conditions which were shown to work in EN07957-76 2016-03-01 14:20; Pd2(DBA)3 (1.05 g) and BINAP (712 mg mg) was stirred in toluene (75 ml). 14:25; 2-bromo-3-methylpyridine (6.94 g), the amine (9.62 g), and sodium t-butoxide (5.43 g), was added to the mixture. 14:30; Heating at 115 °C. In an attempt to degas the reaction by employing vacuum to the flask good reflux, indicating a slight exotherm, took place. HPLC after 5 minutes indicated complet reaction. The mixture was allowed to cool. 2016-03-02 09:00; Water (50 ml) was followowed by 0.5 M citric acid (~75 ml) to give pH 3. The aqueous phase was extracted with another 25 ml toluene and the combined extracts were washed with water. Removal of the solvent in vacuo followed by evaporation of the solvent gave a re
The source
This record comes from experimental reaction archive (ord-2949f6d733cb41eb863993e4ce1f0a88). Open the source and check it against what is on this page.
experimental reaction archive record ord-2949f6d733cb41eb863993e4ce1f0a88 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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