Ethanol → 2-Fluoro-6-(4-octyloxyphenyl)pyrazine

HRID 864264

Reaction equation

HRID 864264 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([F:8])[N:3]=1.[CH2:9]([O:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(=O)([O-])[O-].[Na+].[Na+].C(O)C>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.O>[F:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([C:21]2[CH:22]=[CH:23][C:18]([O:17][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:19][CH:20]=2)[N:3]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 39772844-n-Octyloxyphenylboronic Acid (contains varying amounts of Anhydride)HCID 232733782-Chloro-6-fluoropyrazine

Product 1

HCID 218046342-Fluoro-6-(4-octyloxyphenyl)pyrazineYield 94.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

7.99 g (60.0 mmol) of 2-chloro-6-fluoropyrazine, 15.08 g (60.0 mmol) of 4-octyloxyphenylboronic acid, 12.78 g (120.0 mmol) of sodium carbonate and 0.72 g (0.6 mmol) of tetrakis(triphenylphosphine)palladium(0) are heated at 80° C. for 2 hours in 400 ml of benzene, 300 ml of ethanol and 150 ml of water. The reaction mixture is partitioned between aqueous sodium chloride solution and ether, the organic phase is washed with aqueous sodium chloride solution, dried over sodium sulfate, filtered and freed from the solvents, and the residue is purified by chromatography (silica gel/hexane: ethyl acetate = 8:2). 17.18 g of 2-fluoro-6-(4-octyloxyphenyl)pyrazine are obtained. ##STR15## 1c

Workup

  1. customThe reaction mixture is 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. filtrationfiltered
  5. customthe residue is purified by chromatography (silica gel/hexane: ethyl acetate = 8:2)

Sources & evidence

ORD record
ord-6998e2e71ad14421b508456399b3d2bd
Source dataset
uspto-grants-1996_10
Patent number
US05562859

Linked notes

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