Potassium Carbonate → 3'-[(8-Methyl-8-azabicyclo[3.2.1]oct-3-ylidene)methyl]-3-biphenylcarbonitrile

HRID 564573Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]2[CH2:15][CH:14]3[N:16]([CH3:17])[CH:11]([CH2:12][CH2:13]3)[CH2:10]2)[CH:5]=[CH:6][CH:7]=1.[C:18]([C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1)#[N:19].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O>[CH3:17][N:16]1[CH:14]2[CH2:13][CH2:12][CH:11]1[CH2:10][C:9](=[CH:8][C:4]1[CH:3]=[C:2]([C:24]3[CH:23]=[CH:22][CH:21]=[C:20]([C:18]#[N:19])[CH:25]=3)[CH:7]=[CH:6][CH:5]=1)[CH2:15]2

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 3-[(3-bromophenyl)methylidene]-8-methyl-8-azabicyclo[3.2.1]octane (1.17 g, 4 mmol) in p-dioxane (15 mL) and H2O (5 mL) was added (3-cyanophenyl) boronic acid (0.705 g, 4.80 mmol), Pd(PPh3) (0.185 g, 0.16 mmol), and K2CO3 (1.658 g, 12 mmol) and then the mixture was heated in a microwave oven at 130° C. for 20 min. The organic layer of the reaction mixture was separated, concentrated and purified by Combiflash chromatograph to afford 1.22 g (97%) of the title compound. LC-MS m/z 315 (M+H)+.

Workup

customThe organic layer of the reaction mixture was separated
concentrationconcentrated
custompurified by Combiflash chromatograph

Sources & evidence

ORD record: ord-6851f137603c4d19a8815bb82ece5613
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067408B2

Reaction notes

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