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

HRID 83564
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HRID 83564 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 10340Sodium CarbonateHCID 75806TricyclohexylphosphineHCID 516892Sodium BicarbonateHCID 59162777HCID 59162777, 화합물HCID 86680350HCID 86680350, 화합물

생성물 1

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

시약·촉매·용매

2
HCID 167845palladium(II) acetate촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-5e0a920484c947c786a76dce3afe67a0
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08846746B2

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