Potassium Phosphate, Tribasic → HCID 90416822, compound

HRID 633566Notes

Reaction equation

HRID 633566 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:30][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]>[Br:30][C:31]1[CH:32]=[C:33]2[C:41]([C:6]3[CH:7]=[C:8]([CH2:11][S:12]([CH3:15])(=[O:13])=[O:14])[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:40][N:39]([CH3:43])[C:34]2=[C:35]([O:37][CH3:38])[N:36]=1

Participants

5

Reactant 3

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

Product 1

HCID 90416822HCID 90416822, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

The product from Example 91D (0.058 g, 0.136 mmol), the product from Example 91C (0.05 g, 0.136 mmol), tris(dibenzylideneacetone)dipalladium(0) (3.74 mg, 4.09 μmol), 1,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamante (3.98 mg, 0.014 mmol) and potassium phosphate (0.087 g, 0.409 mmol) were combined and sparged with argon for 15 minutes. Meanwhile a solution of 4:1 dioxane/water (2 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 (0.064 g, 87%).

Workup

  1. customsparged with argon for 15 minutes
  2. customMeanwhile a solution of 4:1 dioxane/water (2 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-9c8d5b1e55514b95b8ead8250cd0920c
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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