Ethanol → 4-(5-(4-Fluoro-phenyl)-pyridine-2-yl)-piperazine-1-carbaldehyde

HRID 32392Notes

Reaction equation

HRID 32392 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH:14]=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.CCO.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[CH:3]=[CH:4][C:5]([N:8]3[CH2:13][CH2:12][N:11]([CH:14]=[O:15])[CH2:10][CH2:9]3)=[N:6][CH:7]=2)=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 231334534-(5-Bromo-pyridine-2-yl)-piperazine-1-carbaldehyde

Product 1

HCID 231334904-(5-(4-Fluoro-phenyl)-pyridine-2-yl)-piperazine-1-carbaldehydeYield 94.7%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 1140TolueneSolvent2×

Procedure

4-(5-Bromo-pyridine-2-yl)-piperazine-1-carbaldehyde (100 mg, 0.37 mmol), 4-Fluorobenzeneboronic acid (55 mg, 0.39 mmol), (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (10 mg, 0.01 mmol), Toluene (2 ml), EtOH (0.5 ml) and 2M Na2CO3 solution (0.5 ml, 1 mmol) were heated at 80° C. under N2 overnight. After cooling the mixture was diluted with toluene and separated. The organic phase was washed with water and brine, filtered through a pad of celite and dried over Na2SO4. The solvent were removed in vacuo affording 100 mg (94%) of the title product as a beige powder.

Workup

  1. temperatureAfter cooling the mixture
  2. customseparated
  3. washThe organic phase was washed with water and brine
  4. filtrationfiltered through a pad of celite
  5. dry with materialdried over Na2SO4
  6. customThe solvent were removed in vacuo

Sources & evidence

ORD record
ord-f097440937804b7ebb6d526c1f0ed005
Source dataset
uspto-grants-2008_09
Patent number
US07427631B2

Reaction notes

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