Potassium Phosphate, Tribasic → HCID 69144654, compound

HRID 444973Notes

Reaction equation

HRID 444973 reaction equation
Cl.[CH2:2]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][C:24](Br)=[CH:23][CH:22]=3)(=[O:20])=[O:19])=[CH:13][N:12]=2)[CH2:7][CH2:6]1)[CH:3]=[CH2:4].[CH:28]1(B(O)O)[CH2:30][CH2:29]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH2:2]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:12]=[CH:13][C:14]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][C:24]([CH:28]4[CH2:30][CH2:29]4)=[CH:23][CH:22]=3)(=[O:20])=[O:19])=[CH:15][CH:16]=2)[CH2:7][CH2:6]1)[CH:3]=[CH2:4]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 54674944HCID 54674944, compound

Product 1

HCID 69144654HCID 69144654, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

398 mg (0.84 mmol) of N-[6-(4-allylpiperazin-1-yl)pyridin-3-yl]-4-bromobenzenesulfonamide from Example 19, 101 mg (1.18 mmol) of cylcopropylboronic acid, 676 mg (3.19 mmol) of K3PO4 and 26 mg (0.09 mmol) of tricyclohexylphosphine were dissolved in 4 ml of toluene and 0.2 ml of water under a nitrogen atmosphere. 10 mg (0.04 mmol) of palladium(II) acetate were then added and the mixture was stirred at 100° C., in a microwave oven, for one hour. After the solvent had been evaporated down to dryness, the resulting residue was treated with water and the mixture was then extracted with ethyl acetate. Because the phases only separated poorly, the finely divided solid was filtered off. The aqueous phase was extracted twice with ethyl acetate. After the combined organic phases had been dried over sodium sulfate and the solvent had been filtered and evaporated down to dryness, the resulting residue was purified by column chromatography.

Workup

  1. customAfter the solvent had been evaporated down to dryness
  2. additionthe resulting residue was treated with water
  3. extractionthe mixture was then extracted with ethyl acetate
  4. customBecause the phases only separated poorly
  5. filtrationthe finely divided solid was filtered off
  6. extractionThe aqueous phase was extracted twice with ethyl acetate
  7. dry with materialAfter the combined organic phases had been dried over sodium sulfate
  8. filtrationthe solvent had been filtered
  9. customevaporated down to dryness
  10. customthe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-1f7210f2c6e1438eaf6ba2f689338db6
Source dataset
uspto-grants-2013_07
Patent number
US08476275B2

Reaction notes

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