3-Bromo-N-methoxy-N-methylbenzamide → N-{2-[(3-bromophenyl)carbonyl]-4,5-dimethoxyphenyl}-2,2-dimethylpropanamide
반응식
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[NH:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15].[Li]CCCC.[Br:24][C:25]1[CH:26]=[C:27]([CH:34]=[CH:35][CH:36]=1)[C:28](N(OC)C)=[O:29]>C1COCC1>[Br:24][C:25]1[CH:26]=[C:27]([C:28]([C:2]2[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=2[NH:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[O:29])[CH:34]=[CH:35][CH:36]=1참가 물질
반응 조건
- 온도
- -78 °C
실험 절차
A flamed dried 500 mL three-necked flask was charged N-(2-bromo-4,5-dimethoxyphenyl)-2,2-dimethylpropanamide (30 g, 95 mmol) and dry THF (200 mL) under N2. n-BuLi (114 mL, 2.5 mol/L, 285 mmol) was added dropwise at −78° C. After the mixture was stirred at −78° C. for 1 hour, 3-bromo-N-methoxy-N-methylbenzamide (23.2 g, 94.9 mmol) in dry THF (30 mL) was added dropwise slowly at −78° C. The resulting mixture was stirred at −78° C. for 3 hours, then quenched with saturated NH4Cl (100 mL). The mixture was exacted with EtOAc (100 mL×3). The combined organic phases were dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column (30:1 hexanes/ethyl acetate) to afford a N-{2-[(3-bromophenyl)carbonyl]-4,5-dimethoxyphenyl}-2,2-dimethylpropanamide as a yellow solid. MS (M+H)=420 and 422.
후처리
- customA flamed dried 500 mL three-necked flask
- stirringThe resulting mixture was stirred at −78° C. for 3 hours
- customquenched with saturated NH4Cl (100 mL)
- dry with materialThe combined organic phases were dried over anhydrous MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column (30:1 hexanes/ethyl acetate)
출처 및 근거
- ORD 기록
- ord-d768d10a66cb4d1aaeab7bc86525be03
- 출처 데이터셋
- uspto-grants-2014_03
- 특허 번호
- US08680116B2
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