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Sodium Carbonate → 5-(3-Butylphenyl)-1-phenyl-1H-pyrazol-3-ylamine

HRID 83564
ノート
印刷プレビュー

反応式

HRID 83564 の反応式
I[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([NH2:13])[CH:3]=1.[CH2:14]([C:18]1[CH:19]=[C:20](B2OC(C)(C)C(C)(C)O2)[CH:21]=[CH:22][CH:23]=1)[CH2:15][CH2:16][CH3:17].C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C(=O)([O-])O.[Na+]>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:14]([C:18]1[CH:23]=[C:22]([C:2]2[N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:5]=[C:4]([NH2:13])[CH:3]=2)[CH:21]=[CH:20][CH:19]=1)[CH2:15][CH2:16][CH3:17]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 10340Sodium CarbonateHCID 75806TricyclohexylphosphineHCID 516892Sodium BicarbonateHCID 59162777HCID 59162777、化合物HCID 86680350HCID 86680350、化合物

生成物 1

HCID 866803825-(3-Butylphenyl)-1-phenyl-1H-pyrazol-3-ylamine収率 86.1%

試薬・触媒・溶媒

2
HCID 167845palladium(II) acetate触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

To a solution of 5-iodo-1-phenyl-1H-pyrazol-3-ylamine (1.00 g) prepared according to the same procedures as Preparation 2 in 1,2-dimethoxyethane (20 ml) were sequentially added 2-(3-butylphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (1.37 g), a 2M aqueous solution of sodium carbonate (10 ml), tricyclohexylphosphine (197 mg) and palladium acetate (79 mg) at room temperature, and the mixture was stirred at reflux for 3 hours. This reaction mixture was cooled to room temperature, a saturated aqueous solution of sodium hydrogen carbonate was added thereto, and then the insoluble substance was filtered off through Celite. The filtrate was extracted with ethyl acetate, the resulting organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1 to 2/3) to give the titled compound (880 mg).

後処理

  1. temperatureat reflux for 3 hours
  2. filtrationthe insoluble substance was filtered off through Celite
  3. extractionThe filtrate was extracted with ethyl acetate
  4. washthe resulting organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1 to 2/3)

出典と根拠

ORDレコード
ord-5e0a920484c947c786a76dce3afe67a0
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08846746B2

反応ノート

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