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

HRID 2059875

반응식

HRID 2059875 반응식
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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매HCID 6344Dichloromethane용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-298cfe593174440d8b9f2ab3d35484b9
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08278316B2

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