Ethyl Acetate → (1-(2-((tert-Butyldimethylsilyl)oxy)ethyl)-1H-pyrazol-3-yl)boronic acid

HRID 511344노트

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HRID 511344 반응식
[B:1]1([C:10]2[NH:14][N:13]=[CH:12][CH:11]=2)[O:5]C(C)(C)C(C)(C)[O:2]1.[C:15]([Si:19]([O:22][CH2:23][CH2:24]I)([CH3:21])[CH3:20])([CH3:18])([CH3:17])[CH3:16].C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>CN(C=O)C.O>[Si:19]([O:22][CH2:23][CH2:24][N:13]1[CH:12]=[CH:11][C:10]([B:1]([OH:2])[OH:5])=[N:14]1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:21])[CH3:20]

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 11129873tert-Butyl(2-iodoethoxy)dimethylsilaneHCID 219315393-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

생성물 1

HCID 67260822(1-(2-((tert-Butyldimethylsilyl)oxy)ethyl)-1H-pyrazol-3-yl)boronic acid

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

In a sealed tube, a suspension of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)-pyrazole (100.0 mg, 0.5154 mmol), tert-butyl-(2-iodoethoxy)-dimethylsilane (196 mg, 0.685 mmol), and Cs2CO3 (271 mg, 0.832 mmol) in DMF (3 mL) was stirred at 100° C. for 16 h. The sample was suspended between EtOAc and water and the layers were separated. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo, giving the title material as the boronic acid, as a yellow oil (203.4 mg). MS (ES+): m/z 270.18/271.13/272.15 (19/79/15) [MH+]. HPLC: tR=3.33 min (CAD, ZQ3, polar—5 min).

후처리

  1. customthe layers were separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-5f6d142848174ee7a1a194b2ecbdfb94
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096624B2

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