Dimethylformamide → 5-Methoxy-3-methyl-pyrrolo[3,2-b]pyridin-1-ylamine
反応式
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([CH3:12])=[CH:10][NH:11][C:6]2=[CH:5][CH:4]=1.[H-].[Na+].C[N:16](C=O)C>>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([CH3:12])=[CH:10][N:11]([NH2:16])[C:6]2=[CH:5][CH:4]=1参加物
反応条件
- 温度
- 0 °C
実験手順
A solution of 5-methoxy-3-methyl-1H-pyrrolo[3,2-b]pyridine (17.3 mmol) in anhydrous DMF (20 mL) is added drop-wise to a stirred solution of NaH (60%, 260 mmol) in anhydrous DMF (35 mL) under N2 at 0° C. for 40 min and then stirred at 0° C. under nitrogen for 30 minutes. HOSA is added portion-wise for 45 minutes at 0° C. and then stirred at 0° C. for 2 hours. After quenching with ice-water (500 mL), the reaction mixture is extracted with ether (3×40 mL). The combined organic layer is washed with water (20 mL) and brine (20 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The residue is purified by silica gel column chromatography eluting with 5-60% EtOAc in heptane to afford 5-methoxy-3-methyl-pyrrolo[3,2-b]pyridin-1-ylamine (1.73 g) as a solid. MS: 178 (M+H); 1H NMR (300 MHz, CDCl3): δ 2.34 (s, 3H), 4.04(s, 3H), 4.75(br, 2N—H), 6.63(d, H), 7.04(s, H), 7.60(d, H).
後処理
- additionHOSA is added portion-wise for 45 minutes at 0° C.
- stirringstirred at 0° C. for 2 hours
- customAfter quenching with ice-water (500 mL)
- extractionthe reaction mixture is extracted with ether (3×40 mL)
- washThe combined organic layer is washed with water (20 mL) and brine (20 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue is purified by silica gel column chromatography
- washeluting with 5-60% EtOAc in heptane
出典と根拠
- ORDレコード
- ord-f4cc4dbece4f4fbf94788621754dcb45
- 出典データセット
- uspto-grants-2012_09
- 特許番号
- US08258130B2
反応ノート
読み込み中…