Potassium Carbonate → HCID 11588431, compound

HRID 2113011Notes

Reaction equation

HRID 2113011 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.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1.[CH:32]1[C:41]2[CH:40]=[CH:39][CH:38]=[C:37](B(O)O)[C:36]=2[CH:35]=[CH:34][N:33]=1>O>[CH:32]1[C:41]2[C:36](=[C:37]([C:15]3[CH:16]=[CH:17][C:12]([O:11][CH2:10][C:6]4[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=4)[C:3]([OH:2])=[O:19])=[CH:13][CH:14]=3)[CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][N:33]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 599474Isoquinoline-5-boronic acidHCID 57643351Methyl 3-((4-iodophenoxy)methyl)benzoate2×

Product 1

HCID 11588431HCID 11588431, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.5 mL of a sonicated and degassed solution of 3-(4-iodo-phenoxymethyl)-benzoic acid methyl ester (of Intermediate 1; 740 mg, 2 mmol), potassium carbonate (830 mg, 6 mmol), bis(tri-cyclohexylphosphine)palladium (available from Strem Chemicals, Inc., Newburyport, Mass.; 70 mg, 0.1 mmol), dioxane (41 mL) and water (4.1 mL) was added to a reaction vial containing 5-isoquinolineboronic acid (available from Frontier Scientific, Inc., Logan, Utah; 104 mg, 0.6 mmol). The solution was sonicated and degassed. The mixture was heated in a microwave oven at 170 degrees for 25 min. The reaction mixture was filtered through 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. The solvents were removed in the Genevac and then 50% aqueous methanol (2 mL) was added. The vial was centrifuged and the solvent removed. This process was repeated and then the same was dried overnight in the oven to give 3-(4-isoquinolin-5-yl-phenoxymethyl)-benzoic acid. Mass spectrum MH+=356.

Workup

  1. custom4.5 mL of a sonicated
  2. additionwas added to a reaction
  3. customThe solution was sonicated
  4. customdegassed
  5. temperatureThe mixture was heated in a microwave oven at 170 degrees for 25 min
  6. filtrationThe reaction mixture was filtered through silica
  7. washwashed with dioxane (1 mL) and dimethylacetamide (1 mL)
  8. addition2 M potassium hydroxide solution (0.4 mL) was added
  9. addition1 M HCl (0.8 mL) was added
  10. customThe solvents were removed in the Genevac
  11. addition50% aqueous methanol (2 mL) was added
  12. customthe solvent removed
  13. customthe same was dried overnight in the oven

Sources & evidence

ORD record
ord-52aff32e0726492183442ad1ed69e4d5
Source dataset
uspto-grants-2009_04
Patent number
US07524870B2

Reaction notes

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