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

HRID 395248Notes

Reaction equation

HRID 395248 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:4][CH:3]=1.[F:15][C:16]1[C:21](B(O)O)=[CH:20][CH:19]=[C:18]([C:25]2[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[CH:27][CH:26]=2)[N:17]=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:15][C:16]1[C:21]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:4][CH:3]=2)=[CH:20][CH:19]=[C:18]([C:25]2[CH:26]=[CH:27][C:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[CH:29][CH:30]=2)[N:17]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27751001-Bromo-4-heptylbenzeneHCID 181728282-Fluoro-6-(4-nonylphenyl)pyridine-3-boronic acid

Product 1

HCID 181728432-Fluoro-3-(4-heptylphenyl)-6-(4-nonylphenyl)pyridineYield 39.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 48 mmol of 1-bromo-4-heptylbenzene in 155 ml of toluene is admixed with 48 mmol of 2-fluoro-6-(4-nonylphenyl)pyridine-3-boronic acid, 77 ml of ethanol, a solution of 96 mmol of sodium carbonate in 77 ml of water and 0.5 mmol of tetrakis(triphenylphosphine)palladium(0) at room temperature. The mixture is heated at the boil for 7 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 sodium 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 as eluent and recrystallization from acetone, giving 8.9 g (39%) of 2-fluoro-3-(4-heptylphenyl)-6-(4-nonylphenyl)pyridine; X 42 S3 56 SC 136.1 S2 136.7 N 137 I.

Workup

  1. customat room temperature
  2. temperatureThe mixture is heated at the boil for 7 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 sodium 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 as eluent
  10. customrecrystallization from acetone

Sources & evidence

ORD record
ord-3e260ea237484a7db87268198e243f6f
Source dataset
uspto-grants-2003_08
Patent number
US06605323B1

Reaction notes

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