Lithium Chloride → HCID 18365300, compound

HRID 380553Notes

Reaction equation

HRID 380553 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1B(O)O.[O:13]([C:20]([N:22]1[CH2:27][CH:26]=[C:25](OS(C(F)(F)F)(=O)=O)[CH2:24][CH:23]1[CH3:36])=[O:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[Li+]>C(COC)OC.C(=O)([O-])[O-].[Na+].[Na+].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[O:13]([C:20]([N:22]1[CH2:27][CH:26]=[C:25]([C:2]2[O:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[CH:3]=2)[CH2:24][CH:23]1[CH3:36])=[O:21])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 3

HCID 433294Lithium ChlorideHCID 2776266Benzo[b]furan-2-boronic acidHCID 21866142HCID 21866142, compound

Product 1

HCID 18365300HCID 18365300, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

A mixture of 2.02 gm (12.5 mMol) benzofuran-2-boronic acid, 3.5 gm (9.6 mMol) 1-phenoxycarbonyl-2-methyl-4-trifluoromethanesulfonyloxy-1,2,3,6-tetrahydropyridine, 0.443 gm (0.38 mMol) tetrakis [triphenylphosphine]-palladium(0), and 1.22 gm (28.8 mMol) lithium chloride in 55 mL dimethoxyethane and 15 mL 2M aqueous sodium carbonate was stirred at reflux for about 18 hours. The reaction mixture was cooled to room temperature and then partitioned between ethyl acetate and aqueous sodium carbonate. The phases were separated and the organic phase was washed with saturated aqueous sodium chloride, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, eluting with hexane containing 10% ethyl acetate. Fractions containing product were combined and concentrated under reduced pressure to provide 2.87 gm (90%) of the desired compound as a light yellow oil.

Workup

  1. temperatureat reflux for about 18 hours
  2. custompartitioned between ethyl acetate and aqueous sodium carbonate
  3. customThe phases were separated
  4. washthe organic phase was washed with saturated aqueous sodium chloride
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washeluting with hexane containing 10% ethyl acetate
  8. additionFractions containing product
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0d3e15a6db034f2a824b8d86381da599
Source dataset
uspto-grants-2001_10
Patent number
US06303627B1

Reaction notes

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