Potassium Carbonate → Tert-butyl 3-(4-bromo-2,5-difluorophenoxy)-2-oxo-1,4'-bipiperidine-1'-carboxylate

HRID 407896Notes

Reaction equation

Br[CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[C:3]1=[O:21].C([O-])([O-])=O.[K+].[K+].[Br:28][C:29]1[C:34]([F:35])=[CH:33][C:32]([OH:36])=[C:31]([F:37])[CH:30]=1>CN(C=O)C.O.CCOC(C)=O>[Br:28][C:29]1[C:34]([F:35])=[CH:33][C:32]([O:36][CH:2]2[CH2:7][CH2:6][CH2:5][N:4]([CH:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]3)[C:3]2=[O:21])=[C:31]([F:37])[CH:30]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of tert-butyl 3-bromo-2-oxo-1,4′-bipiperidine-1′carboxylate (723 mg, 2.00 mmol) in DMF (5 mL) was added K2CO3 (553 mg, 4.00 mmol) and 4-bromo-2,5-difluorophenol (460 mg, 2.20 mmol). The reaction was heated at 60° C. overnight. The reaction was cooled and diluted with water and EtOAc. The organic layer was separated and the aqueous washed with EtOAc. The combined organic layers were dried with MgSO4 and concentrated. The crude residue was purified over silica gel (2:1 hexanes/EtOAc) to give tert-butyl 3-(4-bromo-2,5-difluorophenoxy)-2-oxo-1,4′-bipiperidine-1′-carboxylate (710 mg, 73%) as a white solid.

Workup

temperatureThe reaction was cooled
customThe organic layer was separated
washthe aqueous washed with EtOAc
dry with materialThe combined organic layers were dried with MgSO4
concentrationconcentrated
customThe crude residue was purified over silica gel (2:1 hexanes/EtOAc)

Sources & evidence

ORD record: ord-200bb0d81cbf451086bc699006b70819
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754226B2

Reaction notes

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