Potassium Acetate → (5-formyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazol-4-yl)boronic acid

HRID 2364055노트

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HRID 2364055 반응식
Br[C:2]1[CH:3]=[N:4][N:5]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[C:6]=1[CH:7]=[O:8].CC1(C)C(C)(C)[O:21][B:20](B2OC(C)(C)C(C)(C)O2)[O:19]1.C([O-])(=O)C.[K+]>COCCOC>[CH:7]([C:6]1[N:5]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[N:4]=[CH:3][C:2]=1[B:20]([OH:21])[OH:19])=[O:8]

참가 물질

5

반응물 3

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 247743744-bromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazole-5-carbaldehyde

생성물 1

HCID 86662300(5-formyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazol-4-yl)boronic acid수율 32.3%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

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온도
90 °C

실험 절차

A mixture of 4-bromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazole-5-carbaldehyde (2.00 g, 6.55 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (1.75 g, 6.88 mmol), potassium acetate (1.93 g, 19.7 mmol) and 1,2-dimethoxyethane (40 mL) was purged with argon. Then, 1,1′-bis(diphenylphosphino)ferrocenepalladium (II) dichloride dichloromethane adduct (0.535 g, 0.655 mmol) was added, and the mixture was purged with argon again. The mixture was stirred at 90° C. overnight. After cooled to room temperature, the mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (Purif, silica gel, hexane to 70:30 hexane/EtOAc) to afford the title compound (571 mg, 25%) as a colorless oil:

후처리

  1. customwas purged with argon
  2. customthe mixture was purged with argon again
  3. temperatureAfter cooled to room temperature
  4. filtrationthe mixture was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by column chromatography (Purif, silica gel, hexane to 70:30 hexane/EtOAc)

출처 및 근거

ORD 기록
ord-823b86513d974a7690a293db01e594fe
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691828B2

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