Potassium Carbonate → HCID 11530197, compound

HRID 2113004Notes

Reaction equation

HRID 2113004 reaction equation
C[O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=2)[CH:5]=1.O1CCOCC1.C(=O)([O-])[O-].[K+].[K+].[Cl:32][C:33]1[C:38](B(O)O)=[CH:37][CH:36]=[CH:35][N:34]=1>O>[Cl:32][C:33]1[C:38]([C:15]2[CH:16]=[CH:17][C:12]([O:11][CH2:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:2])=[O:19])=[CH:13][CH:14]=2)=[CH:37][CH:36]=[CH:35][N:34]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 2762704(2-Chloropyridin-3-yl)boronic acidHCID 57643351Methyl 3-((4-iodophenoxy)methyl)benzoate2×

Product 1

HCID 11530197HCID 11530197, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A first stock solution was prepared consisting of 3-(4-iodo-phenoxymethyl)-benzoic acid methyl ester (of Intermediate 1; 1.77 g, 4.8 mmol), bis(tri-cyclohexyl-phosphine)palladium (available from Strem Chemicals, Inc., Newburyport, Mass.; 168 mg, 0.25 mmol), and dioxane (approximately 100 mL). A second stock solution was prepared consisting of potassium carbonate (1.99 g, 14.4 mmol) and water (approximately 10 mL). The solutions were sonicated and degassed by bubbling nitrogen gas through them. 4 mL of the first stock solution and 0.4 mL of the second stock solution were added to a reaction vial containing 2-chloropyridine-3-boronic acid (ASDI Incorporated, Newark, Del.; 94 mg, 0.6 mmol). The mixture was heated in a microwave oven at 170 degrees for 25 min and then passed through a silica gel column (1 g of silica), and washed with dioxane (1 mL) and dimethylacetamide (1 mL). 2 M potassium hydroxide solution (0.4 mL) was added. The mixture was stirred at room temperature overnight, and then 1 M HCl (0.8 mL) was added and the solvents were removed in the Genevac. Aqueous methanol (50%; approximately 2 mL) was added, then the vial was centrifuged and the solvent was removed. This process was repeated and then the sample was dried overnight in the oven to give 3-[4-(2-chloro-pyridin-3-yl)-phenoxymethyl]-benzoic acid. Mass spectrum MH+=340.

Workup

  1. customA first stock solution was prepared
  2. customA second stock solution was prepared
  3. customThe solutions were sonicated
  4. customdegassed
  5. customby bubbling nitrogen gas through them
  6. addition4 mL of the first stock solution and 0.4 mL of the second stock solution were added to a reaction
  7. temperatureThe mixture was heated in a microwave oven at 170 degrees for 25 min
  8. washwashed with dioxane (1 mL) and dimethylacetamide (1 mL)
  9. addition2 M potassium hydroxide solution (0.4 mL) was added
  10. addition1 M HCl (0.8 mL) was added
  11. customthe solvents were removed in the Genevac
  12. additionAqueous methanol (50%; approximately 2 mL) was added
  13. customthe solvent was removed
  14. customthe sample was dried overnight in the oven

Sources & evidence

ORD record
ord-220fc12c0d354c6799a19d981c730728
Source dataset
uspto-grants-2009_04
Patent number
US07524870B2

Reaction notes

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