Sodium Carbonate → HCID 59541817, compound

HRID 2388300Notes

Reaction equation

HRID 2388300 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8](OS(C(F)(F)F)(=O)=O)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH3:19][O:20][C:21]1[C:26](B(O)O)=[CH:25][CH:24]=[CH:23][N:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:26]3[C:21]([O:20][CH3:19])=[N:22][CH:23]=[CH:24][CH:25]=3)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2762709(2-Methoxypyridin-3-yl)boronic acidHCID 114830861,4-Dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate

Product 1

HCID 59541817HCID 59541817, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of trifluoro-methanesulfonic acid 1,4-dioxa-spiro[4.5]dec-7-en-8-yl ester (prepared according to JOC, 69, 3943, 2004, 1.27 g, 3.47 mmol) and 2-methoxypyridine-3-boronic acid (Aldrich, 637 mg, 4.17 mmol) was added tetrakistriphenylphosphine palladium (120 mg, 0.10 mmol), dioxane (10 mL) and aqueous sodium carbonate (4.00 mL, 8.00 mmol, 2N). The reaction mixture was heated to 100° C. under argon for 16 hours and then cooled to room temperature and extracted with ethyl acetate. The organic layer was washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, 0-10% MeOH/CH2Cl2) to afford 3-(1,4-Dioxa-spiro[4.5]dec-7-en-8-yl)-2-methoxy-pyridine as a colorless oil.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (SiO2, 0-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-3f98abe3aa21455791219d4fcddadd8f
Source dataset
uspto-grants-2012_09
Patent number
US08269015B2

Reaction notes

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