1,2-Dimethoxyethane → tert-butyl 4-pyridin-4-yl-3,6-dihydro-2H-pyridine-1-carboxylate

HRID 2403604Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH:12]=1)(=O)=O.[N:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.COCCOC.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[N:10]1([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH:12]=[C:7]([C:25]2[CH:26]=[CH:27][N:22]=[CH:23][CH:24]=2)[CH2:8][CH2:9]1

Participants

Conditions

Temperature: 80 °C

Procedure

Under an argon atmosphere, to a mixture of tert-butyl 4-{[(trifluoromethyl)sulfonyl]oxy}-3,6-dihydropyridine-1(2H)-carboxylate (1.82 g), pyridin-4-yl boronic acid (473 mg), and DME (35 ml) were added tetrakis(triphenylphosphine)palladium (317 mg), cesium carbonate (5.37 g), and water (9 ml), followed by stirring at 80° C. overnight. To the reaction mixture was added water, followed by extraction with EtOAc. The organic layer was dried over MgSO4 and then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain tert-butyl 3,6-dihydro-4,4′-bipyridine-1(2H)-carboxylate (1.28 g).

Workup

extractionfollowed by extraction with EtOAc
dry with materialThe organic layer was dried over MgSO4
customevaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-ea173603311645099151bb24e16c9f9f
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802679B2

Reaction notes

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