Sodium Chloride → HCID 19046968, compound

HRID 1780574Notes

Reaction equation

HRID 1780574 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[N:3]=1.[CH2:9]([O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[C:23](B(O)O)[CH:22]=[CH:21]2)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Na+]>C1C=CC=CC=1.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.CCOCC.O.C(O)C>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:23]2[CH:22]=[CH:21][C:20]3[C:25](=[CH:26][CH:27]=[C:18]([O:17][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:19]=3)[CH:24]=2)[N:3]=1

Participants

10

Reactant 4

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 6394382-Bromo-6-fluoropyridineHCID 19046976HCID 19046976, compound

Product 1

HCID 19046968HCID 19046968, compoundYield 68.7%

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

8.51 g (50 mmol) of 2-bromo-6-fluoropyridine, 14.5 g (50 mmol) of 6-octyloxynaphthalene-2-boronic acid, 1.73 g (1.5 mmol) of tetrakis(triphenylphosphine)palladium(0) and 10.6 g (100 mmol) of sodium carbonate are refluxed in 375 ml of benzene, 250 ml of ethanol and 125 ml of water for 3 hours. The mixture is then distributed between sodium chloride solution and ether, the organic phase is washed with sodium chloride solution, dried over sodium sulfate, concentrated, and the residue is purified by chromatography (silica gel, 9:1 hexane/ethyl acetate), giving 12.08 g of 2-fluoro-6-(6-octyloxynaphth-2-yl)pyridine. ##STR67##

Workup

  1. washthe organic phase is washed with sodium chloride solution
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customthe residue is purified by chromatography (silica gel, 9:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-dd62983642fb4a5eb55acccfac7b341c
Source dataset
uspto-grants-1997_05
Patent number
US05630962

Reaction notes

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