Potassium Carbonate → 2-{1-[Tri(propan-2-yl)silyl]-1H-pyrrol-3-yl}-1,3-thiazole

HRID 746826노트

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HRID 746826 반응식
[CH:1]([Si:4]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[N:5]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6]1)([CH3:3])[CH3:2].Br[C:20]1[S:21][CH:22]=[CH:23][N:24]=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC=CC=1.O.CO>[CH:1]([Si:4]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[N:5]1[CH:9]=[CH:8][C:7]([C:20]2[S:21][CH:22]=[CH:23][N:24]=2)=[CH:6]1)([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 764302-BromothiazoleHCID 27633031-(Triisopropylsilyl)pyrrole-3-boronic acid

생성물 1

HCID 693030142-{1-[Tri(propan-2-yl)silyl]-1H-pyrrol-3-yl}-1,3-thiazole

시약·촉매·용매 1

HCID 21999729HCID 21999729, 화합물용매

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온도
90 °C

실험 절차

A solution of 1-(triisopropylsilyl)-1H-pyrrol-3-ylboronic acid (0.274 g, 0.46 mmol, based on presumed 45% yield of previous step), 2-bromo-1,3-thiazole (0.206 g, 1.2 mmol), potassium carbonate (0.1736, 1.2 mmol), tetrakis(triphenlyphosphine)palladium(0) (0.040 g, 0.035 mmol) in mixed solvent of benzene/water/methanol (10 mL/1 mL/1 mL), was degassed for 5 minutes, then refluxed at 90° C. for overnight. The reaction mixture was quenched with H2O (30 mL), then extracted with EtOAc (3×30 mL) and the combined organic extracts washed with brine. The organic phase was dried over Na2SO4 and concentrated in vacuo. The crude purified by liquid chromatography on silica gel using an ISCO single channel system (Hexane/EtOAc=9/1 to 1/9) to afford 2-[1-(triisopropylsilyl)-1H-pyrrol-3-yl]-1,3-thiazole as a yellow oil.

후처리

  1. customThe reaction mixture was quenched with H2O (30 mL)
  2. extractionextracted with EtOAc (3×30 mL)
  3. washthe combined organic extracts washed with brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude purified by liquid chromatography on silica gel using an ISCO single channel system (Hexane/EtOAc=9/1 to 1/9)

출처 및 근거

ORD 기록
ord-6b25374edd5248cc8700595f4fe778d0
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07393959B2

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