5-(Azidomethyl)isoquinoline → (Isoquinolin-5-yl)methanamine
반응식
[N:1]([CH2:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][N:9]=[CH:10]2)=[N+]=[N-]>CCOC(C)=O.[Pd]>[NH2:1][CH2:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][N:9]=[CH:10]2참가 물질
4
실험 절차
To a solution of 0.0282 g (0.15 mmol) 17 in 1 mL EtOAc was added 0.0034 g Pd (10% on C). After 5 h under H2 at atmospheric pressure, the reaction mixture was diluted with 30 mL EtOAc and filtered over celite. The celite was washed with 200 mL EtOAc, and the filtrate was concentrated in vacuo. Purification by flash chromatography (10×160 mm silica gel, 5% (10% NH40H:MeOH):CH2Cl2) yielded 18. 1H NMR (CDCl3, 400 MHz) δ 9.272 (s, 1H, ArH); 8.583 (d, 1H, J=5.94 Hz, ArH); 7.876 (dd, 2H, J=7.18, 11.57 Hz, ArH); 7.583 (t, 1H, J=7.64 Hz, ArH); MS (Electrospray): m/z 159.0 (M+H).
후처리
- filtrationfiltered over celite
- washThe celite was washed with 200 mL EtOAc
- concentrationthe filtrate was concentrated in vacuo
- customPurification by flash chromatography (10×160 mm silica gel, 5% (10% NH40H:MeOH):CH2Cl2)
출처 및 근거
- ORD 기록
- ord-cc09254dcc88490eb62473c448fbd74e
- 출처 데이터셋
- uspto-grants-2003_03
- 특허 번호
- US06534510B2
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