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

HRID 1747813ノート

反応式

HRID 1747813 の反応式
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

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 5

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)触媒HCID 962Water溶媒2 回HCID 1140Toluene溶媒HCID 516892Sodium Bicarbonate溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-eb3e4e029e5b4b15b88a55422355d6cf
出典データセット
uspto-grants-2015_10
特許番号
US09150588B2

反応ノート

読み込み中…