Potassium Carbonate → 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]acetamide

HRID 1752567

반응식

HRID 1752567 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.Br[CH2:16][C:17]([NH2:19])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][C:2]1([CH3:14])[C:6]([CH3:7])([CH3:8])[O:5][B:4]([C:9]2[CH:13]=[N:12][N:11]([CH2:16][C:17]([NH2:19])=[O:18])[CH:10]=2)[O:3]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

생성물 1

HCID 569657342-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]acetamide

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
50 °C

실험 절차

A suspension of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (2.00 g, 10.3 mmol), 2-bromoacetamide (2.14 g, 15.5 mmol), and potassium carbonate (2.14 g, 15.5 mmol) in acetone (60 mL) was heated at about 50° C. for about 3.5 days. The reaction mixture was then cooled to ambient temperature, filtered through diatomaceous earth, while washing with additional acetone, and then concentrated under reduced pressure. The crude material was then dissolved in a minimal amount of dichloromethane and purified via silica gel chromatography eluting with a gradient of 80-100% ethyl acetate in heptane to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.88 (s, 1H), 7.57 (s, 1H), 7.46 (s, 1H), 7.24 (s, 1H), 4.77 (s, 2H), 1.26 (s, 12H). MS (ESI+) m/z 252.2 (M+H)+.

후처리

  1. temperatureThe reaction mixture was then cooled to ambient temperature
  2. filtrationfiltered through diatomaceous earth
  3. washwhile washing with additional acetone
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe crude material was then dissolved in a minimal amount of dichloromethane
  6. custompurified via silica gel chromatography
  7. washeluting with a gradient of 80-100% ethyl acetate in heptane

출처 및 근거

ORD 기록
ord-ae4889e1f97041278ba99d4f3d34ae01
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09163007B2

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