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[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([B:10]([OH:12])[OH:11])[CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH2:15]1COCC1.CI>>[CH3:15][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([B:10]([OH:12])[OH:11])[CH:8]=2)[CH:3]=[CH:2]1참가 물질
5
실험 절차
A mixture of indole-6-boronic acid (0.100 g, 0.615 mmol), sodium hydride (0.07 g, 20 mmol) and THF (5 mL, 60 mmol) was stirred at rt for 20 min. then methyl iodide (100 μL, 20 mmol) was added and the mixture was allowed ro stir at rt for 3 hours. The reaction was quenched with sat. NH4Cl solution, washed with brine and dried over Na2SO4, then the solvent was removed in vacuo. The crude product was purified by chromatography over silica gel eluting with 1:9 EtOAc/hexane and 1% MeOH, yielding the desired product. 1H NMR (400 MHz, CDCl3) δ ppm 3.99 (s, 3H), 6.58 (m, 1H). 7.23 (m, 1H), 7.81 (m, 1H), 8.08 (m, 1H) and 8.34 (m, 1H). MS (ES+): m/z 176.15 [MH+].
후처리
- stirringstir at rt for 3 hours
- customThe reaction was quenched with sat. NH4Cl solution
- washwashed with brine
- dry with materialdried over Na2SO4
- customthe solvent was removed in vacuo
- customThe crude product was purified by chromatography over silica gel eluting with 1:9 EtOAc/hexane and 1% MeOH
출처 및 근거
- ORD 기록
- ord-09daf3b50e1b4a9f96c7ad8df91b639c
- 출처 데이터셋
- uspto-grants-2010_04
- 특허 번호
- US07700594B2
연결된 노트
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