Potassium Carbonate → tert-butyl 2-(5'-bromo-3,4,5,6-tetrahydro-2H-[1,2]bipyridinyl-4-yl)ethylcarbamate

HRID 1019694

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[NH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:11][CH2:10]2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 130 °C

Procedure

10.37 g (43.80 mmol) of 2,5-dibromopyridine, 10.00 g (43.80 mmol) of tert-butyl 2-piperidin-4-ylethylcarbamate and 6.05 g (43.80 mmol) of potassium carbonate are placed in an autoclave. The mixture is then heated at 130° C. for 12 hours. The reaction mixture is allowed to cool to room temperature and then taken up in chloroform and saturated aqueous sodium hydrogen carbonate solution. The aqueous phase is separated out and extracted twice with chloroform, and the combined organic phases are washed with saturated aqueous sodium chloride solution and dried over sodium sulfate, and the filtrate is concentrated under reduced pressure.

Workup

temperatureto cool to room temperature
customThe aqueous phase is separated out
extractionextracted twice with chloroform
washthe combined organic phases are washed with saturated aqueous sodium chloride solution
dry with materialdried over sodium sulfate
concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record: ord-dab2bd828e60411a9ec5e24385c50ac9
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716289B2

Linked notes

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