5-(Azidomethyl)isoquinoline → (Isoquinolin-5-yl)methanamine
反応式
[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]2参加物
4
実験手順
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).
後処理
- 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)
出典と根拠
- ORDレコード
- ord-cc09254dcc88490eb62473c448fbd74e
- 出典データセット
- uspto-grants-2003_03
- 特許番号
- US06534510B2
反応ノート
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