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

HRID 2364055ノート

反応式

HRID 2364055 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

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:

後処理

  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)

出典と根拠

ORDレコード
ord-823b86513d974a7690a293db01e594fe
出典データセット
uspto-grants-2014_04
特許番号
US08691828B2

反応ノート

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