Methanol → 1-(Triisopropylsilyl)pyrrole-3-boronic acid

HRID 746825

반응식

HRID 746825 반응식
Br[C:2]1[CH:6]=[CH:5][N:4]([Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9])[CH:3]=1.C([Li])(C)(C)C.C[O:23][B:24](OC)[O:25]C.CO>C1COCC1.O>[CH:8]([Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[N:4]1[CH:5]=[CH:6][C:2]([B:24]([OH:25])[OH:23])=[CH:3]1)([CH3:10])[CH3:9]

참가 물질

7

반응물 4

HCID 887MethanolHCID 8470Trimethyl borateHCID 27633023-Bromo-1-(triisopropylsilyl)pyrroleHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 27633031-(Triisopropylsilyl)pyrrole-3-boronic acid

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To −78° C. solution of 3-bromo-1-(triisopropylsilyl)-1H-pyrrole (0.619 g, 2.288 mmol) in 10 mL THF was added tert-butyllithium (2.83 mL of 1.7 M in Heptane, 4.80 mmol) dropwise. The reaction mixture was stirring at −78° C. for 45 minutes, then trimethylborate (2.38 g, 22.88 mmol) was added. The reaction was stirred for another 45 minutes at −78° C. To this was then added 0.9 mL methanol and water solution (V/V=1:1) and the reaction was allowed warm to room temperature. 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, and used in the next step without further purification.

후처리

  1. stirringThe reaction was stirred for another 45 minutes at −78° C
  2. temperaturethe reaction was allowed warm to room temperature
  3. customThe reaction mixture was quenched with H2O (30 mL)
  4. extractionextracted with EtOAc (3×30 mL)
  5. washthe combined organic extracts washed with brine
  6. dry with materialThe organic phase was dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customused in the next step without further purification

출처 및 근거

ORD 기록
ord-f3c9ff7386824966b7599ee99336e74b
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07393959B2

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