Dichloromethane → 2-Chloro-4-(4-chlorophenyl)-3,4'-bipyridine

HRID 2101315

Reaction equation

Br[C:2]1[C:3]([Cl:15])=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.CC1(C)C(C)(C)OB([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)O1.ClCCl.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1COCC1.CCOC(C)=O.O>[Cl:15][C:3]1[C:2]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)=[C:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[CH:6]=[CH:5][N:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

In a pressure tube, to a stirring solution of 3-bromo-2-chloro-4-(4-chlorophenyl)pyridine (1.3 g, 4.49 mmol) in THF (60 mL) at room temperature under argon was added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (2.3 g, 11.21 mmol), 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride complex with dichloromethane (350 mg, 0.43 mmol), and powdered K3PO4 (1.9 g, 8.96 mmol). The resulting suspension was stirred and heated at 100° C. under argon for 12 h. After the reaction mixture was cooled to room temperature, water (40 mL) and EtOAc (50 mL) were added. The layers were separated. The organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel column eluting with 20% ethyl acetate-hexanes) to isolate 850 mg of the title compound as a white solid. HPLC/MS: retention time=2.157 min, [M+H]+=301.

Workup

temperatureAfter the reaction mixture was cooled to room temperature
customThe layers were separated
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude product was purified by flash chromatography (silica gel column eluting with 20% ethyl acetate-hexanes)

Sources & evidence

ORD record: ord-691bb2c0b93c4b33a3e01d8eef584046
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572808B2

Linked notes

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