Lithium Chloride → HCID 17785791, compound

HRID 380550Notes

Reaction equation

HRID 380550 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1B(O)O.[O:14]([C:21]([N:23]1[CH2:28][CH:27]=[C:26](OS(C(F)(F)F)(=O)=O)[CH2:25][CH:24]1[CH3:37])=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[Li+]>C(=O)([O-])[O-].[Na+].[Na+].C(COC)OC.C(OCC)(=O)C.C1(P(C2[C-](Cl)C=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2].[Pd+2]>[O:14]([C:21]([N:23]1[CH2:28][CH:27]=[C:26]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[CH2:25][CH:24]1[CH3:37])=[O:22])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

8

Reactant 3

HCID 433294Lithium ChlorideHCID 2734375(Naphthalen-2-yl)boronic acidHCID 21866142HCID 21866142, compound

Product 1

HCID 17785791HCID 17785791, compoundYield 50%

Reagents, catalysts & solvents 4

HCID 178477923HCID 178477923, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent2×

Procedure

A mixture of 5.46 gm (31.8 mMol) naphthalene-2-boronic acid, 8.28 gm (22.7 mMol) 1-phenoxycarbonyl-2-methyl-4-trifluoromethanesulfonyloxy-1,2,3,6-tetrahydropyridine, 0.741 gm (0.91 mMol) palladium(II) diphenylphosphino-ferrocenyl chloride, and 2.88 gm (68 mMol) lithium chloride in 25 mL 2M aqueous sodium carbonate and 96 mL dimethoxyethane was heated at reflux for about 18 hours. The reaction mixture was cooled to room temperature and was diluted with ethyl acetate and saturated 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 3.87 gm (50%) of the title compound as a viscous oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for about 18 hours
  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-5e88f03dc4e340caba12340807ccb66e
Source dataset
uspto-grants-2001_10
Patent number
US06303627B1

Reaction notes

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