Lithium Chloride → HCID 57485796, compound

HRID 749142Notes

Reaction equation

HRID 749142 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]2[CH2:15][CH:12]([CH2:13][CH:14]=1)[CH2:11][N:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:9]2)(=O)=O.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25](B(O)O)[CH:24]=1.[Cl-].[Li+]>C(COC)OC.C(=O)([O-])[O-].[Na+].[Na+]>[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:7]2[CH:8]3[CH2:15][CH:12]([CH2:13][CH:14]=2)[CH2:11][N:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:9]3)[CH:24]=1

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 27343783-Pyridinylboronic acidHCID 57486352HCID 57486352, compound

Product 1

HCID 57485796HCID 57485796, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

A mixture of ethyl 6-trifluoromethanesulfonyloxy-3-azabicyclo[3.3.1] non-6-ene-3-carboxylate (270 mg, 0.790 mmol) in 6 mL of dimethoxyethane, 1.5 mL of saturated sodium carbonate solution, 3-pyridineboronic acid (146 mg, 1.20 mmol) and lithium chloride (99 mg, 2.37 mmol) was degassed and placed under an argon atmosphere (5 min purge). Tetrakis(triphenyphosphine)palladium(0) (60 mg) was added, and the reaction mixture was heated at reflux for 4 h. It was then cooled and filtered though a plug of silica gel, eluting with ethyl acetate. Concentration of the filtrate and column chomatography of the residue, with a gradient of 0-5% methanol in dichloromethane, gave a yellow oil (130 mg, 60%).

Workup

  1. customwas degassed
  2. custom(5 min purge)
  3. additionTetrakis(triphenyphosphine)palladium(0) (60 mg) was added
  4. temperaturethe reaction mixture was heated
  5. temperatureat reflux for 4 h
  6. temperatureIt was then cooled
  7. filtrationfiltered though a plug of silica gel
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-113451fd2f9443b4ab50ce66ae1db93f
Source dataset
uspto-grants-2008_07
Patent number
US07402592B2

Reaction notes

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