3-Bromopyridine → tert-butyl (3R)-3-methyl-4-pyridin-3-ylpiperazine-1-carboxylate
Reaction equation
Brc1cccnc1.C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1>C1COCCO1.CC(=O)O.CC(=O)O.CC(C)Oc1cccc(OC(C)C)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.O=C([O-])[O-].[Cs+].[Cs+].[Pd]>C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1cccnc1Participants
7
Conditions
- Temperature
- 100 °C
Procedure
diacetoxypalladium (9.34 mg, 0.04 mmol) and RuPhos (0.039 g, 0.08 mmol) were suspended in 1,4 dioxane (5 mL), degassed and stirred at 50 °C for 10 minutes. Then (R)-tert-butyl 3-methylpiperazine-1-carboxylate (0.100 g, 0.50 mmol), 3-bromopyridine (0.040 mL, 0.42 mmol) and cesium carbonate (0.203 g, 0.62 mmol) were added and the reaction mixture was stirred at 100 °C for 16 h. LCMS showed only 5% conversion to desired product. This was part of a screen and Ruphos, sodium tert-butoxide in toluene gave far better conversion so this was abandoned.
Sources & evidence
- ORD record
- ord-a21d6ec12c02473a98dce7de6b637849
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Reaction notes
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