Ethanol → 5-Bromo-3-fluoro-2-(4-octyloxyphenyl)pyridine

HRID 1757353Notes

Reaction equation

HRID 1757353 reaction equation
Br[C:2]1[C:7]([F:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.[CH2:10]([O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1(C)C=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.O>[Br:9][C:5]1[CH:6]=[C:7]([F:8])[C:2]([C:22]2[CH:23]=[CH:24][C:19]([O:18][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:20][CH:21]=2)=[N:3][CH:4]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 39772844-n-Octyloxyphenylboronic Acid (contains varying amounts of Anhydride)HCID 224128322,5-Dibromo-3-fluoropyridine

Product 1

HCID 193875465-Bromo-3-fluoro-2-(4-octyloxyphenyl)pyridineYield 70%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

12.74 g (50.00 mmol) of 2,5-dibromo-3-fluoropyridine, 12.51 g (50.00 mmol) of 4-octyloxybenzeneboronic acid, 0.58 g (0.50 mmol) of tetrakis(triphenylphosphine)palladium(0) and 10.60 g (100 mmol) of sodium carbonate are heated at 80° C. for 3 hours in 375 ml of toluene, 250 ml of ethanol and 125 ml of water. The mixture is subsequently partitioned between aqueous sodium chloride solution and ether, and the organic phase is washed with aqueous sodium chloride solution, dried over sodium sulfate, evaporated and purified by chromatography (silica gel/hexane : ethyl acetate =9:1), giving 13.31 g of 5-bromo-3-fluoro-2-(4-octyloxyphenyl)pyridine. ##STR15##

Workup

  1. customThe mixture is subsequently partitioned between aqueous sodium chloride solution and ether
  2. washthe organic phase is washed with aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. custompurified by chromatography (silica gel/hexane : ethyl acetate =9:1)

Sources & evidence

ORD record
ord-fbb22c8b5b6d4cdb8d6e696932880612
Source dataset
uspto-grants-1995_08
Patent number
US05445763

Reaction notes

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