Potassium Carbonate → HCID 69663052, compound

HRID 2212091Notes

Reaction equation

HRID 2212091 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1.[C:18]1([S:24]([C:27]([CH3:39])([CH3:38])[CH2:28][CH2:29][CH2:30][N:31]2[CH2:36][C:35](Br)=[CH:34][CH2:33][CH2:32]2)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCOCC1>[C:18]1([S:24]([C:27]([CH3:39])([CH3:38])[CH2:28][CH2:29][CH2:30][N:31]2[CH2:32][C:33]([C:12]3[CH:13]=[CH:14][C:9]([O:8][CH3:7])=[CH:10][CH:11]=3)=[CH:34][CH2:35][CH2:36]2)(=[O:26])=[O:25])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 69663010HCID 69663010, compound

Product 1

HCID 69663052HCID 69663052, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

2M Potassium carbonate solution (containing tetra-n-butylammonium hydroxide) (0.25 ml) followed by 4-methoxybenzeneboronic acid (0.056 g; 0.37 mmol) was added to a solution of Example 229 (0.095 g; 0.25 mmol) in 1,4-dioxane (6 ml). The solution was deoxygenated with nitrogen at room temperature for 5 minutes. Tetrakistriphenylphosphine palladium(0) (catalytic) was added and the solution stirred for 30 minutes at 80° C. After cooling to room temperature, ethyl acetate was added and the organic phase separated then washed twice with water. The organic layer was dried (MgSO4) and evaporated in vacuo. Purification using an SCX cartridge eluting with 1/9 NH3/MeOH afforded the title compound as a yellow oil (90 mg, 87%).

Workup

  1. customThe solution was deoxygenated with nitrogen at room temperature for 5 minutes
  2. additionTetrakistriphenylphosphine palladium(0) (catalytic) was added
  3. temperatureAfter cooling to room temperature
  4. additionethyl acetate was added
  5. customthe organic phase separated
  6. washthen washed twice with water
  7. dry with materialThe organic layer was dried (MgSO4)
  8. customevaporated in vacuo
  9. customPurification
  10. washeluting with 1/9 NH3/MeOH

Sources & evidence

ORD record
ord-c118436664b2446695a0010be5ee3598
Source dataset
uspto-grants-2006_09
Patent number
US07101892B2

Reaction notes

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