Potassium Phosphate, Tribasic → 5-(4-(Trifluoromethyl)phenyl)pyridazin-3(2H)-one

HRID 2059875

Reaction equation

HRID 2059875 reaction equation
C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.I[C:21]1[CH:26]=[N:25][NH:24][C:23](=[O:27])[CH:22]=1.[F:28][C:29]([F:40])([F:39])[C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:28][C:29]([F:40])([F:39])[C:30]1[CH:35]=[CH:34][C:33]([C:21]2[CH:26]=[N:25][NH:24][C:23](=[O:27])[CH:22]=2)=[CH:32][CH:31]=1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 166383305-Iodo-2,3-dihydropyridazin-3-one

Product 1

HCID 579503875-(4-(Trifluoromethyl)phenyl)pyridazin-3(2H)-oneYield 39.1%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

Tricyclohexyl phosphine (16.6 μL, 0.02 mmol) was added to a mixture of 5-iodopyridazin-3(2H)-one (35 mg, 0.16 mmol), 4-(trifluoromethyl)phenylboronic acid (30 mg, 0.16 mmol), potassium phosphate tribasic (117 mg, 0.55 mmol), and palladium (II) acetate (3.5 mg, 0.02 mmol) in Toluene (0.8 mL) and Water (0.3 mL). The mixture was stirred at 100° C. for 22 hours. The reaction was diluted with CH2Cl2, filtered and concentrated. The crude was purified using HPLC (Phen Luna Axia C18 5μ 10:90:0.1 to 90:10:0.1 MeOH—H2O-TFA) to afford the desired product 5-(4-(trifluoromethyl)phenyl)pyridazin-3(2H)-one 18A (14.8 mg, 0.06 mmol, 39.1% yield) as a white solid. LC/MS 282 (M+H)+, tR 0.77 min (method 5).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe crude was purified

Sources & evidence

ORD record
ord-298cfe593174440d8b9f2ab3d35484b9
Source dataset
uspto-grants-2012_10
Patent number
US08278316B2

Linked notes

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