Di-tert-butyl dicarbonate → 4-Boc-1-(5-bromo-2-pyridyl)piperazine
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.[O:14](C(OC(C)(C)C)=O)[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:9][CH2:10][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:14])[CH2:12][CH2:13]2)=[N:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of compound 90a (125 g, 516 mmol) in DCM (300 mL), TEA (104 g, 1.03 mol) was added, followed by (BOC)2O (135 g, 619 mmol) in portions with stirring at 0° C. The resulting mixture was stirred overnight at room temperature. The reaction was then quenched with water (100 mL), and the product was extracted with DCM (3×150 mL). The combined organic layers were concentrated under reduced pressure to obtain compound 90b as a white solid (125 g, 71% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C14H20BrN3O2: 342.1 (M+H). found 342.1.
Workup
- stirringThe resulting mixture was stirred overnight at room temperature
- customThe reaction was then quenched with water (100 mL)
- extractionthe product was extracted with DCM (3×150 mL)
- concentrationThe combined organic layers were concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-6f6d225d61ec4d4abe6078388980decf
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09249163B2
Reaction notes
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