Potassium Phosphate, Tribasic → HCID 90415835, compound

HRID 633573Notes

Reaction equation

HRID 633573 reaction equation
[CH3:1][C:2]1[C:6](B(O)O)=[C:5]([CH3:10])[O:4][N:3]=1.Br[C:12]1[CH:13]=[C:14]2[C:22]([C:23]3[CH:28]=[C:27]([CH2:29][S:30]([CH3:33])(=[O:32])=[O:31])[CH:26]=[CH:25][C:24]=3[O:34][C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][C:36]=3[F:42])=[CH:21][N:20]([CH3:43])[C:15]2=[C:16]([O:18][CH3:19])[N:17]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:42][C:36]1[CH:37]=[C:38]([F:41])[CH:39]=[CH:40][C:35]=1[O:34][C:24]1[CH:25]=[CH:26][C:27]([CH2:29][S:30]([CH3:33])(=[O:31])=[O:32])=[CH:28][C:23]=1[C:22]1[C:14]2[C:15](=[C:16]([O:18][CH3:19])[N:17]=[C:12]([C:6]3[C:2]([CH3:1])=[N:3][O:4][C:5]=3[CH3:10])[CH:13]=2)[N:20]([CH3:43])[CH:21]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 90416822HCID 90416822, compound

Product 1

HCID 90415835HCID 90415835, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
60 °C

Procedure

3,5-dimethylisoxazole-4-boronic acid (0.016 g, 0.112 mmol), the product from Example 91E (0.05 g, 0.093 mmol), tris(dibenzylideneacetone)dipalladium(0) (2.56 mg, 2.79 μmol), 1,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamante (2.72 mg, 9.30 μmol) and potassium phosphate (0.059 g, 0.279 mmol) were combined and sparged with argon for 15 minutes. Meanwhile a solution of 4:1 dioxane/water (0.8 mL) was sparged with N2 for 15 minutes and transferred by syringe into the reaction vessel under argon. The mixture was heated at 60° C. for 2 hours and partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous Na2SO4), treated with 3-mercaptopropyl functionalized silica gel, filtered, and concentrated to afford the title compound (0.052 g, 100%).

Workup

  1. customsparged with argon for 15 minutes
  2. customMeanwhile a solution of 4:1 dioxane/water (0.8 mL) was sparged with N2 for 15 minutes
  3. customtransferred by syringe into the reaction vessel under argon
  4. custompartitioned between ethyl acetate and water
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried (anhydrous Na2SO4)
  7. additiontreated with 3-mercaptopropyl functionalized silica gel
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0d28848bd89d4ade9e78f5763a2f8f83
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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