tert-Butyl piperazine-1-carboxylate → HCID 58913155, compound
Reaction equation
CC(C)(C)OC(=O)N1CCNCC1.CC(C)(C)OC(=O)n1ccc2cccc(Br)c21>C1COCCO1.CC(=O)O.CC(=O)O.CC(C)Oc1cccc(OC(C)C)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.O=C([O-])[O-].[Cs+].[Cs+].[Pd]>CC(C)(C)OC(=O)N1CCN(c2cccc3ccn(C(=O)OC(C)(C)C)c23)CC1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 95 °C
Procedure
_Trial reaction_ Palladium (II) acetate (7.58 mg, 0.03 mmol) and 2-Dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl (31.5 mg, 0.07 mmol) were suspended in 1,4-dioxane (1 mL) at ambient temperature. The mixture was degassed and purged with nitrogen and warmed to 50°C for 20 mins. In a separate vessel, were mixed tert-butyl piperazine-1-carboxylate (62.9 mg, 0.34 mmol), tert-butyl 7-bromo-1H-indole-1-carboxylate (100 mg, 0.34 mmol) and cesium carbonate (165 mg, 0.51 mmol) in 1,4-dioxane (2 mL). The mixture was degassed and purged with nitrogen several times. The catalyst solution was added and the resulting mixture was heated at 95°C overnight under a nitrogen atmosphere. No reaction observed by LCMS. Main component of the mixture was unreacted BOC- protected indole. No loss of BOC, but still no reaction.
Sources & evidence
- ORD record
- ord-5c1e7b0afe1e4c2ea268d161da8ff7be
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Reaction notes
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