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]1참가 물질
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
- temperatureThe reaction mixture was then cooled to ambient temperature
- filtrationfiltered through diatomaceous earth
- washwhile washing with additional acetone
- concentrationconcentrated under reduced pressure
- dissolutionThe crude material was then dissolved in a minimal amount of dichloromethane
- custompurified via silica gel chromatography
- washeluting with a gradient of 80-100% ethyl acetate in heptane
출처 및 근거
- ORD 기록
- ord-e96d4c89e5674c97bfbd420af7951106
- 출처 데이터셋
- uspto-grants-2014_02
- 특허 번호
- US08648069B2
연결된 노트
불러오는 중…