Triphenylphosphine → HCID 21933958, compound

HRID 891424Notes

Reaction equation

HRID 891424 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:20][C:21]1[CH:22]=[C:23]([N:28]2[C:33](=[O:34])[C:32]([O:35][CH2:36][CH2:37][CH2:38][CH3:39])=[C:31](Cl)[CH:30]=[N:29]2)[CH:24]=[CH:25][C:26]=1[F:27].[CH3:41][S:42][C:43]1[CH:48]=[CH:47][C:46](B(O)O)=[CH:45][CH:44]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)(C)C>[F:20][C:21]1[CH:22]=[C:23]([N:28]2[C:33](=[O:34])[C:32]([O:35][CH2:36][CH2:37][CH2:38][CH3:39])=[C:31]([C:46]3[CH:47]=[CH:48][C:43]([S:42][CH3:41])=[CH:44][CH:45]=3)[CH:30]=[N:29]2)[CH:24]=[CH:25][C:26]=1[F:27]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 62657Potassium Phosphate, TribasicHCID 27339594-(Methylthio)phenylboronic acidHCID 21933852HCID 21933852, compound

Product 1

HCID 21933958HCID 21933958, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent2×

Conditions

Temperature
70 °C

Procedure

A slurry of palladium(II) acetate (9.0 mg, 0.04 mmol), triphenylphosphine (21.0 mg, 0.08 mmol) and isopropanol (1 mL) was stirred at room temperature for 10 minutes. To this mixture was added 2-(3,4-Difluorophenyl)-4-(1-butoxy)-5-chloro-3(2H)-pyridazinone (Example 536A, 0.63 g, 2 mmol), 4-(methylthio)benzeneboronic acid (0.403 mg, 2.4 mmol) and isopropanol (4 mL). A solution of K3PO4 (0.66 g, 3 mmol) in water (1 mL) was also added and the resulting reaction mixture was deoxygenated by bubbling nitrogen through it for 2 minutes. The reaction mixture was then stirred under a nitrogen atmosphere for 15 hours at 70° C. The reaction mixture was then cooled to room temperature and water (15 mL) was added to provide a precipitate. The precipitate was collected by filtration and rinsed with water then hexane to give after drying the title compound (0.77 g, 95%).

Workup

  1. customthe resulting reaction mixture
  2. customwas deoxygenated
  3. customby bubbling nitrogen through it for 2 minutes
  4. temperatureThe reaction mixture was then cooled to room temperature
  5. additionwater (15 mL) was added
  6. customto provide a precipitate
  7. filtrationThe precipitate was collected by filtration
  8. washrinsed with water
  9. customhexane to give
  10. dry with materialafter drying the title compound (0.77 g, 95%)

Sources & evidence

ORD record
ord-398a2b329ac0444a89ff262fdf922bf8
Source dataset
uspto-grants-2006_02
Patent number
US07001895B2

Reaction notes

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