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Cesium carbonate → Methyl 2-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrazol-1-yl)propanoate

HRID 1627548
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HRID 1627548 반응식
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.[CH3:15][O:16][C:17](=[O:22])[C:18](Br)([CH3:20])[CH3:19].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:15][O:16][C:17](=[O:22])[C:18]([CH3:20])([N:12]1[CH:13]=[C:9]([B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]2)[CH:10]=[N:11]1)[CH3:19]
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참가 물질

5

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HCID 10796Cesium carbonateHCID 90097Methyl 2-bromo-2-methylpropionateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

생성물 1

HCID 59599416Methyl 2-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrazol-1-yl)propanoate수율 63%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

To a solution of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (5 g, 25.77 mmol) and 2-bromo-2-methyl-propionic acid methyl ester (12.6 g, 27.06 mmol) in DMF (85 mL), was added Cs2CO3 (12.6 g, 38.65 mmol). The reaction mixture was heated to 90° C. in an oil bath overnight. The reaction solution was cooled to room temperature, and partitioned between water and ethyl acetate. The combined ethyl acetate solution was washed with water five times, dried over Na2SO4, and concentrated to give the product 2-methyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazol-1-yl]propionic acid methyl ester (4.776 g, 63% yield).

후처리

  1. temperatureThe reaction solution was cooled to room temperature
  2. custompartitioned between water and ethyl acetate
  3. washThe combined ethyl acetate solution was washed with water five times
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-dc4f02ec942a4a949fe55a6fbd70c38a
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08785632B2

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