Potassium Carbonate → 1,1-Dimethylethyl 4-[(3'-cyano-3-biphenylyl)methylidene]-1-piperidinecarboxylate

HRID 564568

Reaction equation

HRID 564568 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1.[C:22]([C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1)#[N:23].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O>[C:22]([C:24]1[CH:29]=[C:28]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]=[C:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]3)[CH:3]=2)[CH:27]=[CH:26][CH:25]=1)#[N:23]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 57813409Tert-butyl 4-(3-bromobenzylidene)piperidine-1-carboxylate

Product 1

HCID 670058691,1-Dimethylethyl 4-[(3'-cyano-3-biphenylyl)methylidene]-1-piperidinecarboxylateYield 85.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 1,1-dimethylethyl 4-[(3-bromophenyl)methylidene]-1-piperidinecarboxylate (2.07 g, 5.88 mmol) in p-dioxane (30 mL) and H2O (10 mL) was added (3-cyanophenyl)boronic acid (1.036 g, 7.05 mmol), Pd(PPh3) (0.272 g, 0.235 mmol), and K2CO3 (2.436 g, 17.63 mmol) and then the reaction was heated in a microwave at 130° C. for 15 minutes. The organic layer of the reaction mixture was separated, concentrated and purified by Combiflash chromatograph to afford 1.88 g (85%) of the title compound. LC-MS m/z 749 (2M+H)+.

Workup

  1. customThe organic layer of the reaction mixture was separated
  2. concentrationconcentrated
  3. custompurified by Combiflash chromatograph

Sources & evidence

ORD record
ord-a05dac54005349b08cf1ad8f9d50ee1c
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Linked notes

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