Ethanol → 2-Fluoro-6-(4-nonylphenyl)-3-(4-pentylphenyl)pyridine

HRID 395247Notes

Reaction equation

HRID 395247 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1.[F:13][C:14]1[C:19](B(O)O)=[CH:18][CH:17]=[C:16]([C:23]2[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:25][CH:24]=2)[N:15]=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:13][C:14]1[C:19]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=2)=[CH:18][CH:17]=[C:16]([C:23]2[CH:24]=[CH:25][C:26]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:27][CH:28]=2)[N:15]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27355991-Bromo-4-pentylbenzeneHCID 181728282-Fluoro-6-(4-nonylphenyl)pyridine-3-boronic acid

Product 1

HCID 181728352-Fluoro-6-(4-nonylphenyl)-3-(4-pentylphenyl)pyridine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 40 mmol of 1 -bromo-4-pentylbenzene in 90 ml of toluene is admixed with 44 mmol of 2-fluoro-6-(4-nonylphenyl)pyridine-3-boronic acid, 45 ml of ethanol, a solution of 80 mmol of sodium carbonate in 45 ml of water and 0.4 mmol of tetrakis(triphenylphosphine)palladium(0) at room temperature. The mixture is heated at the boil for 5 h. After cooling, the phases are separated, the aqueous phase is extracted with tert-butyl methyl ether and the combined organic phases are washed with water and saturated sodium chloride solution and dried with magnesium sulfate. The solvents are then removed under reduced pressure and the raw product is purified by column chromatography over silica gel 60 using n-heptane/dichloromethane 1:1 as eluent and recrystallization from acetonitrile/acetone 1:1, giving 2-fluoro-6-(4-nonylphenyl)-3-(4-pentylphenyl)pyridine.

Workup

  1. customat room temperature
  2. temperatureThe mixture is heated at the boil for 5 h
  3. temperatureAfter cooling
  4. customthe phases are separated
  5. extractionthe aqueous phase is extracted with tert-butyl methyl ether
  6. washthe combined organic phases are washed with water and saturated sodium chloride solution
  7. dry with materialdried with magnesium sulfate
  8. customThe solvents are then removed under reduced pressure
  9. customthe raw product is purified by column chromatography over silica gel 60 using n-heptane/dichloromethane 1:1 as eluent
  10. customrecrystallization from acetonitrile/acetone 1:1

Sources & evidence

ORD record
ord-cf230074a1fa40879a14cb9926152c99
Source dataset
uspto-grants-2003_08
Patent number
US06605323B1

Reaction notes

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