반응식
[NH2:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[CH2:13][NH:12][C:11](=[O:14])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].Br[C:16]1[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[O:14]=[C:11]1[NH:12][CH2:13][C@@H:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([NH:1][C:16]3[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=3[C:18]([O:20][CH3:21])=[O:19])[CH:3]=2)[CH2:10]1참가 물질
반응물 4
생성물 1
시약·촉매·용매 2
반응 조건
- 온도
- 100 °C
실험 절차
To a mixture of (4R)-4-(3-amino-4-chlorophenyl)pyrrolidin-2-one (0.18 g, 0.86 mmol), methyl 2-bromobenzoate (0.37 g, 1.72 mmol), palladium acetate (0.038 g, 0.172 mmol), and Buchwald's reagent (2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl) (0.122 g, 0.256 mmol) was added dioxane (2 mL). The mixture was degassed by alternatively applying a vacuum and flushing with nitrogen for a few cycles. After 15 minutes, potassium carbonate (0.237 g, 1.72 mmol) was added. The mixture was stirred overnight at 100° C., and then cooled to room temperature and filtered through Celite. The filtrate was washed with an aqueous HCl solution and extracted with ethyl acetate (3 times). The ethyl acetate layers were then washed with brine and concentrated to give the title compound (13a) as a brown residue which was used directly in the next step. MS (ESI) m/z 345 (M+H)+.
후처리
- customThe mixture was degassed
- customflushing with nitrogen for a few cycles
- temperaturecooled to room temperature
- filtrationfiltered through Celite
- washThe filtrate was washed with an aqueous HCl solution
- extractionextracted with ethyl acetate (3 times)
- washThe ethyl acetate layers were then washed with brine
- concentrationconcentrated
출처 및 근거
- ORD 기록
- ord-b990302f28e646dc9060359215fe48a8
- 출처 데이터셋
- uspto-grants-2013_01
- 특허 번호
- US08344028B2
연결된 노트
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