Potassium Phosphate, Tribasic → HCID 90416585, compound

HRID 633571Notes

Reaction equation

HRID 633571 reaction equation
[F:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][C:6]=1B1OC(C)(C)C(C)(C)O1.Br[C:31]1[CH:32]=[C:33]2[C:41](I)=[CH:40][N:39]([CH3:43])[C:34]2=[C:35]([O:37][CH3:38])[N:36]=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:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:9][C:10]=1[C:41]1[C:33]2[C:34](=[C:35]([O:37][CH3:38])[N:36]=[C:31]([C:6]3[CH:7]=[C:8]([CH2:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:9]=[CH:10][C:5]=3[O:4][C:3]3[CH:25]=[CH:26][C:27]([F:29])=[CH:28][C:2]=3[F:1])[CH:32]=2)[N:39]([CH3:43])[CH:40]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 89657473HCID 89657473, compoundHCID 90417079HCID 90417079, compound

Product 1

HCID 90416585HCID 90416585, compoundYield 12.6%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

The product from Example 91D (1.233 g, 2.180 mmol), the product from Example 91C (0.8 g, 2.180 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.060 g, 0.065 mmol), 1,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamante (0.064 g, 0.218 mmol) and potassium phosphate (1.388 g, 6.54 mmol) were combined and sparged with argon for 15 minutes. Meanwhile a solution of 4:1 dioxane/water (18 mL) was sparged with nitrogen for 15 minutes and transferred by syringe into the reaction vessel under argon. The mixture was stirred for 2 hours at ambient temperature, 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. Purification by chromatography (silica gel, 10-50% ethyl acetate in heptanes) afforded the title compound (0.104 g, 6%).

Workup

  1. customsparged with argon for 15 minutes
  2. customMeanwhile a solution of 4:1 dioxane/water (18 mL) was sparged with nitrogen 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
  10. customPurification by chromatography (silica gel, 10-50% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-1d104e0e406e4c15aa6216e4d14110bd
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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