Potassium Carbonate → 1-(cyclopropylmethyl)-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one

HRID 1747813노트

반응식

HRID 1747813 반응식
Cl[C:2]1[C:7](=[O:8])[C:6]([O:9][CH3:10])=[CH:5][N:4]([CH2:11][CH:12]2[CH2:14][CH2:13]2)[N:3]=1.[C:15]1([N:21]2[C:25](B3OC(C)(C)C(C)(C)O3)=[CH:24][CH:23]=[N:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O.C(=O)([O-])O.[Na+].[Cl-].[Na+].O.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[CH:12]1([CH2:11][N:4]2[CH:5]=[C:6]([O:9][CH3:10])[C:7](=[O:8])[C:2]([C:25]3[N:21]([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:22]=[CH:23][CH:24]=3)=[N:3]2)[CH2:14][CH2:13]1

참가 물질

9

반응물 3

HCID 11430Potassium CarbonateHCID 580723671-Phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 895861593-chloro-1-(cyclopropylmethyl)-5-methoxypyridazin-4(1H)-one

생성물 1

HCID 680148501-(cyclopropylmethyl)-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one수율 59.6%

시약·촉매·용매 5

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)촉매HCID 962Water용매2회HCID 1140Toluene용매HCID 516892Sodium Bicarbonate용매HCID 57417360Sodium chloride; water용매

실험 절차

3-Chloro-1-(cyclopropylmethyl)-5-methoxypyridazin-4(1H)-one (0.133 g), 1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.200 g), potassium carbonate (0.171 g) and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.0219 g) were suspended in toluene (3.09 mL) and water (0.309 mL), and the suspension was heated under reflux for 20 hr under an argon atmosphere. The reaction mixture was cooled to room temperature, diluted with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered, concentrated, purified by NH silica gel column chromatography (ethyl acetate/hexane→methanol/ethyl acetate) and recrystallized from ethyl acetate/hexane to give the title compound (0.119 g).

후처리

  1. temperatureunder reflux for 20 hr under an argon atmosphere
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by NH silica gel column chromatography (ethyl acetate/hexane→methanol/ethyl acetate)
  7. customrecrystallized from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-eb3e4e029e5b4b15b88a55422355d6cf
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150588B2

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