반응식
C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][N:55]=1.[O:60]1[CH:65]([C:66]([O:68][CH2:69][CH3:70])=[O:67])[CH2:64][NH:63][C:62]2[CH:71]=[CH:72][CH:73]=[CH:74][C:61]1=2>O1CCOCC1.O.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[N:55]1[CH:56]=[CH:57][CH:58]=[CH:59][C:54]=1[N:63]1[CH2:64][CH:65]([C:66]([O:68][CH2:69][CH3:70])=[O:67])[O:60][C:61]2[CH:74]=[CH:73][CH:72]=[CH:71][C:62]1=2참가 물질
반응물 4
생성물 1
시약·촉매·용매 3
반응 조건
- 온도
- 100 °C
실험 절차
In a sealable tube, tris(dibenzylideneacetone) dipalladium (0) (5.2 mg, 0.0056 mmol), (S)-BINAP (10.7 mg, 0.017 mmol), cesium carbonate (132 mg, 0.41 mmol), 2-bromopyridine (33 □L, 0.35 mmol), and ethyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxylate (Example 3a, 60 mg, 0.29 mmol) were dissolved in dioxane (2 mL). The reaction vessel was sealed and the suspension was heated at 100° C. for 20 h. The reaction mixture was cooled to ambient temperature, diluted with water (15 mL), and the product was extracted with dichloromethane (3×20 mL). The organic fractions were dried over sodium sulfate and concentrated. Purification of the product by flash column chromatography (15% to 25% EtOAc/hexane) afforded the title compound (46 mg, 0.16 mmol). MS m/z: 285 (M+1).
후처리
- customThe reaction vessel was sealed
- temperatureThe reaction mixture was cooled to ambient temperature
- extractionthe product was extracted with dichloromethane (3×20 mL)
- dry with materialThe organic fractions were dried over sodium sulfate
- concentrationconcentrated
- customPurification of the product by flash column chromatography (15% to 25% EtOAc/hexane)
출처 및 근거
- ORD 기록
- ord-51e9447c75b04d669f08eb89eb40d763
- 출처 데이터셋
- uspto-grants-2011_01
- 특허 번호
- US07872009B2
연결된 노트
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