4-Bromoaniline → 4-(1-isobutyl-1H-pyrazol-4-yl)aniline

HRID 873568노트

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HRID 873568 반응식
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH2:9]([N:13]1[CH:17]=[C:16](B2OC(C)(C)C(C)(C)O2)[CH:15]=[N:14]1)[CH:10]([CH3:12])[CH3:11].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl.O1CCCC1.CO.O>[CH2:9]([N:13]1[CH:17]=[C:16]([C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=2)[CH:15]=[N:14]1)[CH:10]([CH3:12])[CH3:11]

참가 물질

6

반응물 3

HCID 78074-BromoanilineHCID 10340Sodium CarbonateHCID 27593921-Isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

생성물 1

HCID 633283934-(1-isobutyl-1H-pyrazol-4-yl)aniline

시약·촉매·용매 2

HCID 178418807HCID 178418807, 화합물촉매HCID 21892291Methanol tetrahydrofuran water용매

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온도
85 °C

실험 절차

A suspension of 4-bromoaniline (406 mg, 2.362 mmol), 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (650 mg, 2.60 mmol), PdCl2(dppf)-dichloromethane adduct (57.9 mg, 0.071 mmol) and sodium carbonate (526 mg, 4.96 mmol) in a 6:2:1 mixture of tetrahydrofuran/methanol/water (12 ml) was taken through three vacuum/nitrogen purge cycles; and the reaction mixture was heated in an oil bath at 85° C. overnight. The mixture was diluted with ethyl acetate and water; the separated aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine, dried with magnesium sulfate, filtered and concentrated. The residue was purified by normal phase chromatography to give the title compound.

후처리

  1. custompurge cycles
  2. additionThe mixture was diluted with ethyl acetate and water
  3. extractionthe separated aqueous layer was extracted with ethyl acetate
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by normal phase chromatography

출처 및 근거

ORD 기록
ord-17f19f6eeb524441b70562349a4e2f84
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975398B2

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