Potassium Phosphate, Tribasic → HCID 16752626, compound

HRID 1260218Notes

Reaction equation

HRID 1260218 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C@@H:18]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH3:25])[CH2:19]3)=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH:26]1(B(O)O)[CH2:28][CH2:27]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:26]1([C:2]2[CH:3]=[CH:4][C:5]([S:8]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([C@@H:18]4[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH3:25])[CH2:19]4)=[CH:14][CH:13]=3)(=[O:9])=[O:10])=[CH:6][CH:7]=2)[CH2:28][CH2:27]1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 57470071HCID 57470071, compound

Product 1

HCID 16752626HCID 16752626, compoundYield 24.2%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

0.3 g of 4-bromo-N-[4-((S)-1-propyl-pyrrolidin-3-yl)-phenyl]-benzenesulfonamide (0.71 mmol), 0.079 g of cyclopropylboronic acid (0.92 mmol), 0.526 g of potassium phosphate (2.48 mmol) and 0.02 g of ricyclohexylphosphin were dissolved in a mixture of 4 ml of toluene and 2 ml of water. After addition of 0.008 g of palladium(II)-acetate (0.04 mmol), the reaction mixture was stirred for 1 h at 100° C. in the microwave (CEM). The solution was decanted, the remaining suspension containing the catalyst washed again with ethyl acetate, the combined solvent extracts evaporated to dryness, redissolved in ethyl acetate and washed with water. The aqueous phase was reextracted once with ethyl acetate, the organic layers combined, dried over magnesium sulfate, filtered and evaporated under reduced pressure. The crude product was purified via silica gel chromatogrphay with dichloromethane, dichloromethane-methanol (5.5%). Fractions containing the product were combined, the solvent removed, to yield 0.066 g of the title product.

Workup

  1. customThe solution was decanted
  2. additionthe remaining suspension containing the catalyst
  3. washwashed again with ethyl acetate
  4. customthe combined solvent extracts evaporated to dryness
  5. dissolutionredissolved in ethyl acetate
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe crude product was purified via silica gel chromatogrphay with dichloromethane, dichloromethane-methanol (5.5%)
  11. additionFractions containing the product
  12. customthe solvent removed

Sources & evidence

ORD record
ord-7670786630cc4b4abc60a85b508b1500
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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