Potassium Carbonate → 1,1-Dimethylethyl 3′,6′-dihydro[3,4′-bipyridine]-1′(2′H)-carboxylate

HRID 2403594Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH:14]=2)O1.Br[C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:26]1[CH:27]=[CH:28][CH:29]=[C:24]([C:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:13][CH:14]=2)[CH:25]=1

Participants

Conditions

Temperature: 80 °C

Procedure

tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate (400 mg) and 3-bromopyridine (226 mg) were dissolved in DMF (4 ml), and K2CO3 (536 mg) and a 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride-dichloromethane complex were added, followed by stirring at 80° C. overnight. The reaction mixture was concentrated under reduced pressure, and then a saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with CHCl3. The organic layer was dried over Na2SO4 and the solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/MeOH) to obtain tert-butyl 3′,6′-dihydro-3,4′-bipyridine-1′(2′H)-carboxylate (249 mg).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
additiona saturated aqueous sodium hydrogen carbonate solution was added
extractionfollowed by extraction with CHCl3
dry with materialThe organic layer was dried over Na2SO4
concentrationthe solvent was concentrated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record: ord-be58d75e8c5b4ab5be852778041ca059
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802679B2

Reaction notes

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